CH617653A5 - Process for the preparation of cyclobutane derivatives. - Google Patents
Process for the preparation of cyclobutane derivatives. Download PDFInfo
- Publication number
- CH617653A5 CH617653A5 CH1133775A CH1133775A CH617653A5 CH 617653 A5 CH617653 A5 CH 617653A5 CH 1133775 A CH1133775 A CH 1133775A CH 1133775 A CH1133775 A CH 1133775A CH 617653 A5 CH617653 A5 CH 617653A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- iii
- zinc
- chloro
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 230000008569 process Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 9
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000011701 zinc Substances 0.000 claims description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
- 229910052725 zinc Inorganic materials 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 25
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 17
- -1 haloacyl halide Chemical class 0.000 claims description 17
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 16
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical class O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims description 16
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 11
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 10
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001345 alkine derivatives Chemical class 0.000 claims description 9
- 150000001983 dialkylethers Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 238000002474 experimental method Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- 150000001923 cyclic compounds Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 229940126062 Compound A Drugs 0.000 description 18
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 18
- 150000004820 halides Chemical class 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000001266 acyl halides Chemical class 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000006352 cycloaddition reaction Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- DFLRGCFWSRELEL-UHFFFAOYSA-N cyclobut-2-en-1-one Chemical class O=C1CC=C1 DFLRGCFWSRELEL-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- WGZNOUWVAIGKDI-UHFFFAOYSA-N 2-chloroethenone Chemical compound ClC=C=O WGZNOUWVAIGKDI-UHFFFAOYSA-N 0.000 description 5
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- SZZWLAZADBEDQP-UHFFFAOYSA-N 1,2-dimethylcyclopentene Chemical compound CC1=C(C)CCC1 SZZWLAZADBEDQP-UHFFFAOYSA-N 0.000 description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000251730 Chondrichthyes Species 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- 238000007157 ring contraction reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GQUXMDLPOJYAQR-UHFFFAOYSA-N 4-chloro-2,2,3,3-tetramethylcyclobutan-1-one Chemical compound CC1(C)C(Cl)C(=O)C1(C)C GQUXMDLPOJYAQR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000005695 dehalogenation reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- DZSNJASVIURWOG-UHFFFAOYSA-N 2,4-dimethylpenta-2,3-diene Chemical compound CC(C)=C=C(C)C DZSNJASVIURWOG-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- AYRARFPNJWKFJO-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-propan-2-ylidenecyclobutan-1-one Chemical compound CC(C)=C1C(=O)C(Cl)C1(C)C AYRARFPNJWKFJO-UHFFFAOYSA-N 0.000 description 2
- WNUHQMBBZGXNRN-UHFFFAOYSA-N 2-chloro-3,4-dimethylcyclobutan-1-one Chemical compound CC1C(C)C(=O)C1Cl WNUHQMBBZGXNRN-UHFFFAOYSA-N 0.000 description 2
- ODJKQDQTDZLQML-UHFFFAOYSA-N 4-(2,5-dimethylhex-4-en-3-yloxy)-2,5-dimethylhex-2-ene Chemical compound C(C)(C)C(C=C(C)C)OC(C=C(C)C)C(C)C ODJKQDQTDZLQML-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- AUKRLLQRIPIBMF-UHFFFAOYSA-N [4-methyl-2-(4-methyl-1-phenylpent-3-en-2-yl)oxypent-3-enyl]benzene Chemical compound C(C1=CC=CC=C1)C(C=C(C)C)OC(C=C(C)C)CC1=CC=CC=C1 AUKRLLQRIPIBMF-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical compound C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VOVOITCISSQINJ-VXNVDRBHSA-N (2s,4s)-2-chloro-3,3-dimethyl-4-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=C[C@@H]1C(=O)[C@@H](Cl)C1(C)C VOVOITCISSQINJ-VXNVDRBHSA-N 0.000 description 1
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 1
- VFCHHMABGOYOQI-SOFGYWHQSA-N (e)-2,4-dimethylhex-3-ene Chemical compound CC\C(C)=C\C(C)C VFCHHMABGOYOQI-SOFGYWHQSA-N 0.000 description 1
- FHHSSXNRVNXTBG-VOTSOKGWSA-N (e)-3-methylhex-3-ene Chemical compound CC\C=C(/C)CC FHHSSXNRVNXTBG-VOTSOKGWSA-N 0.000 description 1
- IFDRDSWHWMTLKM-UHFFFAOYSA-N 1,3,3-triphenylpropa-1,2-dienylbenzene Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 IFDRDSWHWMTLKM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 1
- JIEJJGMNDWIGBJ-UHFFFAOYSA-N 1-propan-2-yloxypropane Chemical compound CCCOC(C)C JIEJJGMNDWIGBJ-UHFFFAOYSA-N 0.000 description 1
- VQCORKJNHWCDFL-UHFFFAOYSA-N 10-ethenylidenenonadecane Chemical compound CCCCCCCCCC(=C=C)CCCCCCCCC VQCORKJNHWCDFL-UHFFFAOYSA-N 0.000 description 1
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 1
- PBVXKUXNZJUZQV-UHFFFAOYSA-N 2,2-dichloroacetyl bromide Chemical compound ClC(Cl)C(Br)=O PBVXKUXNZJUZQV-UHFFFAOYSA-N 0.000 description 1
- PEWNTOXFFHXOND-UHFFFAOYSA-N 2,2-dichlorobutanoyl chloride Chemical compound CCC(Cl)(Cl)C(Cl)=O PEWNTOXFFHXOND-UHFFFAOYSA-N 0.000 description 1
- TVWWMKZMZALOFP-UHFFFAOYSA-N 2,2-dichloroethenone Chemical compound ClC(Cl)=C=O TVWWMKZMZALOFP-UHFFFAOYSA-N 0.000 description 1
- IPKCHUGFUGHNRZ-UHFFFAOYSA-N 2,2-dichloropropanoyl chloride Chemical compound CC(Cl)(Cl)C(Cl)=O IPKCHUGFUGHNRZ-UHFFFAOYSA-N 0.000 description 1
- HUASXBAJMQJHCZ-UHFFFAOYSA-N 2,2-dimethyl-3-(propan-2-yloxymethyl)cyclopropane-1-carboxylic acid Chemical compound CC(C)OCC1C(C(O)=O)C1(C)C HUASXBAJMQJHCZ-UHFFFAOYSA-N 0.000 description 1
- WLRIGHMLOSYTOU-UHFFFAOYSA-N 2,2-dimethyl-3-propan-2-ylidenecyclopropane-1-carboxylic acid Chemical class CC(C)=C1C(C(O)=O)C1(C)C WLRIGHMLOSYTOU-UHFFFAOYSA-N 0.000 description 1
- SZFRZEBLZFTODC-UHFFFAOYSA-N 2,3,4-trimethylpent-2-ene Chemical compound CC(C)C(C)=C(C)C SZFRZEBLZFTODC-UHFFFAOYSA-N 0.000 description 1
- CXLNYETYUQMZKI-UHFFFAOYSA-N 2,3-dimethyl-1h-indene Chemical compound C1=CC=C2CC(C)=C(C)C2=C1 CXLNYETYUQMZKI-UHFFFAOYSA-N 0.000 description 1
- WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical compound CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 1
- YFOKREQYTOOZCQ-UHFFFAOYSA-N 2,8-dimethylnona-4,5-diene Chemical compound CC(C)CC=C=CCC(C)C YFOKREQYTOOZCQ-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- FGEAOSXMQZWHIQ-UHFFFAOYSA-N 2-chloro-2-phenylacetyl chloride Chemical compound ClC(=O)C(Cl)C1=CC=CC=C1 FGEAOSXMQZWHIQ-UHFFFAOYSA-N 0.000 description 1
- VJYQGFFRTRZHIM-UHFFFAOYSA-N 2-chloro-3,3,4-trimethylcyclobutan-1-one Chemical compound ClC1C(C(C1(C)C)C)=O VJYQGFFRTRZHIM-UHFFFAOYSA-N 0.000 description 1
- VOVOITCISSQINJ-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=CC1C(=O)C(Cl)C1(C)C VOVOITCISSQINJ-UHFFFAOYSA-N 0.000 description 1
- XEGIYMUGTDAQFJ-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(phenylmethoxymethyl)cyclobutan-1-one Chemical compound CC1(C)C(Cl)C(=O)C1COCC1=CC=CC=C1 XEGIYMUGTDAQFJ-UHFFFAOYSA-N 0.000 description 1
- PQQUGMKIQAFPOI-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(propan-2-yloxymethyl)cyclobutan-1-one Chemical compound CC(C)OCC1C(=O)C(Cl)C1(C)C PQQUGMKIQAFPOI-UHFFFAOYSA-N 0.000 description 1
- FMNSXKUPJVNBAL-UHFFFAOYSA-N 2-chloro-3,3-dimethylcyclobutan-1-one Chemical compound CC1(C)CC(=O)C1Cl FMNSXKUPJVNBAL-UHFFFAOYSA-N 0.000 description 1
- NBAWXLZPDZZSGA-UHFFFAOYSA-N 2-chloro-3-methylcyclobutan-1-one Chemical compound CC1CC(=O)C1Cl NBAWXLZPDZZSGA-UHFFFAOYSA-N 0.000 description 1
- DZYVVFYOJBNORV-UHFFFAOYSA-N 2-chloro-4-ethyl-3,3-dimethylcyclobutan-1-one Chemical compound CCC1C(=O)C(Cl)C1(C)C DZYVVFYOJBNORV-UHFFFAOYSA-N 0.000 description 1
- CXZZAVRCAQDNPD-UHFFFAOYSA-N 2-chloro-4-methylcyclobutan-1-one;prop-1-ene Chemical compound CC=C.CC1CC(Cl)C1=O CXZZAVRCAQDNPD-UHFFFAOYSA-N 0.000 description 1
- KVQJVAOMYWTLEO-UHFFFAOYSA-N 2-chlorobutanoyl chloride Chemical compound CCC(Cl)C(Cl)=O KVQJVAOMYWTLEO-UHFFFAOYSA-N 0.000 description 1
- JEQDSBVHLKBEIZ-UHFFFAOYSA-N 2-chloropropanoyl chloride Chemical compound CC(Cl)C(Cl)=O JEQDSBVHLKBEIZ-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NHWDWRFEZJEQAI-UHFFFAOYSA-N 3,5-diethylhepta-3,4-diene Chemical compound CCC(CC)=C=C(CC)CC NHWDWRFEZJEQAI-UHFFFAOYSA-N 0.000 description 1
- PQWJEAQPDQVJHE-UHFFFAOYSA-N 3-(3-carboxybut-2-en-2-yl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(=C(C)C(=O)O)C1C(C1(C)C)C(=O)O PQWJEAQPDQVJHE-UHFFFAOYSA-N 0.000 description 1
- OXMWLXYKDKRADR-UHFFFAOYSA-N 3-ethyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CCC1C(C(O)=O)C1(C)C OXMWLXYKDKRADR-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical compound CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 description 1
- BEQGRRJLJLVQAQ-UHFFFAOYSA-N 3-methylpent-2-ene Chemical compound CCC(C)=CC BEQGRRJLJLVQAQ-UHFFFAOYSA-N 0.000 description 1
- ZSGJOTZSPLCGAT-UHFFFAOYSA-N 4-chloro-2,2,3-trimethylcyclobutan-1-one Chemical compound CC1C(Cl)C(=O)C1(C)C ZSGJOTZSPLCGAT-UHFFFAOYSA-N 0.000 description 1
- ZOMAVUNDAPMWTK-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclobutan-1-one Chemical compound CC(C)=CC1C(Cl)C(=O)C1(C)C ZOMAVUNDAPMWTK-UHFFFAOYSA-N 0.000 description 1
- XAPUHLONFQTWSY-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-3-(phenylmethoxymethyl)cyclobutan-1-one Chemical compound C(C1=CC=CC=C1)OCC1C(C(C1(C)C)=O)Cl XAPUHLONFQTWSY-UHFFFAOYSA-N 0.000 description 1
- TWKNAOLSKWSFIZ-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-3-(propan-2-yloxymethyl)cyclobutan-1-one Chemical compound ClC1C(C(C1COC(C)C)(C)C)=O TWKNAOLSKWSFIZ-UHFFFAOYSA-N 0.000 description 1
- LTDUHFPLNKOMFC-UHFFFAOYSA-N 4-chloro-2,2-dimethylcyclobutan-1-one Chemical compound CC1(C)CC(Cl)C1=O LTDUHFPLNKOMFC-UHFFFAOYSA-N 0.000 description 1
- BBEJKLYWJWHPDE-UHFFFAOYSA-N 4-chloro-3-ethyl-2,2-dimethylcyclobutan-1-one Chemical compound CCC1C(Cl)C(=O)C1(C)C BBEJKLYWJWHPDE-UHFFFAOYSA-N 0.000 description 1
- NEYLAVKYYZDLIN-UHFFFAOYSA-N 5-methylhexa-1,2-diene Chemical compound CC(C)CC=C=C NEYLAVKYYZDLIN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- VGPUUFZKLLOIDD-UHFFFAOYSA-N ethyl 2,3,5-trimethylhexa-2,4-dienoate Chemical compound CCOC(=O)C(C)=C(C)C=C(C)C VGPUUFZKLLOIDD-UHFFFAOYSA-N 0.000 description 1
- HUKZSTOEZTYETR-UHFFFAOYSA-N ethyl 3-(4-chloro-2,2-dimethyl-3-oxocyclobutyl)-2-methylbut-2-enoate Chemical compound ClC1C(C(C1C(=C(C)C(=O)OCC)C)(C)C)=O HUKZSTOEZTYETR-UHFFFAOYSA-N 0.000 description 1
- MJLDTSREPDUTSV-UHFFFAOYSA-N ethyl 3-chloro-1,2-dimethyl-2-(2-methylprop-1-enyl)-4-oxocyclobutane-1-carboxylate Chemical compound CCOC(=O)C1(C)C(=O)C(Cl)C1(C)C=C(C)C MJLDTSREPDUTSV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QKEOZZYXWAIQFO-UHFFFAOYSA-M mercury(1+);iodide Chemical compound [Hg]I QKEOZZYXWAIQFO-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- QIRVGKYPAOQVNP-UHFFFAOYSA-N methylidenecyclobutane Chemical compound C=C1CCC1 QIRVGKYPAOQVNP-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- PODAMDNJNMAKAZ-UHFFFAOYSA-N penta-2,3-diene Chemical compound CC=C=CC PODAMDNJNMAKAZ-UHFFFAOYSA-N 0.000 description 1
- SFKKCPDHVKBQFJ-UHFFFAOYSA-N pentadeca-1,2-diene Chemical compound CCCCCCCCCCCCC=C=C SFKKCPDHVKBQFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- NGKSKVYWPINGLI-UHFFFAOYSA-N prop-2-ynylbenzene Chemical compound C#CCC1=CC=CC=C1 NGKSKVYWPINGLI-UHFFFAOYSA-N 0.000 description 1
- WEHMXWJFCCNXHJ-UHFFFAOYSA-N propa-1,2-dienylbenzene Chemical compound C=C=CC1=CC=CC=C1 WEHMXWJFCCNXHJ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FTJHRVWWPKMONX-UHFFFAOYSA-N propylidenecyclopropane Chemical compound CCC=C1CC1 FTJHRVWWPKMONX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/517—Saturated compounds containing a keto group being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3864474A GB1524682A (en) | 1974-09-04 | 1974-09-04 | Process for the preparation of cyclobutanones |
| GB2181475 | 1975-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617653A5 true CH617653A5 (en) | 1980-06-13 |
Family
ID=26255536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1133775A CH617653A5 (en) | 1974-09-04 | 1975-09-02 | Process for the preparation of cyclobutane derivatives. |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5912093B2 (xx) |
| BR (1) | BR7505619A (xx) |
| CH (1) | CH617653A5 (xx) |
| DD (1) | DD124724A5 (xx) |
| DE (1) | DE2539048A1 (xx) |
| FR (1) | FR2299302A1 (xx) |
| HU (1) | HU176610B (xx) |
| IL (1) | IL48032A (xx) |
| IT (1) | IT1042237B (xx) |
| NL (1) | NL186314C (xx) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638356A1 (de) * | 1976-08-26 | 1978-03-02 | Bayer Ag | Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeureester |
| FI780930A (fi) * | 1977-03-31 | 1978-10-01 | Ciba Geigy Ag | Foerfarande foer framstaellning av 2-(2'2'2'-trihalogenetyl)-4-halogencyklobutan-1-oner de medelst foerfarandet framstaellda produkterna och deras anvaendning samt de foer deras framstaellning anvaenda mellanprodukterna |
| FI780931A (fi) * | 1977-03-31 | 1978-10-01 | Ciba Geigy | 2-(2'2'-dihalogenvinyl)-och 2-(2'2'2'-trihalogenetyl)-cyklobutanoner foerfarande foer deras framstaellning och deras anvaendning |
| EP0002207B1 (de) * | 1977-11-24 | 1981-09-02 | Ciba-Geigy Ag | Dichlorvinylcyclobutanone, Verfahren zu deren Herstellung und ihre Verwendung als Zwischenprodukte für die Herstellung von Schädlingsbekämpfungsmitteln |
| FR2438022A2 (fr) * | 1978-10-02 | 1980-04-30 | Ciba Geigy Ag | Procede de preparation de cyclobutanones halogenees |
| JPS5553234A (en) * | 1978-10-11 | 1980-04-18 | Ciba Geigy Ag | 22*2**2**2**tribromoethyl**44chlorocyclobutanee 11one*its manufacture and intermediate for manufacture |
| JPS5692830A (en) * | 1979-12-07 | 1981-07-27 | Ciba Geigy Ag | 22*2**2**dichloroo3**3**3**trifluoropropyl** and 22*2**2**3**trichloroo3**3** difluoropropyl**44chlorocyclobutanee11one and their manufacture |
| DE3042218A1 (de) * | 1980-11-08 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | 2,2-dimethylcyclobutanone, und verfahren zu ihrer herstellung |
| US5420356A (en) * | 1993-08-11 | 1995-05-30 | Sumitomo Chemical Company, Limited | Process for producing cyclobutanones |
| EP3766862B1 (en) | 2019-07-17 | 2023-06-07 | Shin-Etsu Chemical Co., Ltd. | Dimethylcyclobutanone compounds, dimethylcyclobutane compounds, and processes for preparing the same |
| EP3766861B1 (en) | 2019-07-17 | 2023-05-24 | Shin-Etsu Chemical Co., Ltd. | Diester compound having a dimethylcyclobutane ring, a process for preparing the same, and a process for preparing dimethylcyclobutane compound derived from the diester compound |
-
1975
- 1975-08-29 HU HU75SE1794A patent/HU176610B/hu unknown
- 1975-09-02 IL IL48032A patent/IL48032A/xx unknown
- 1975-09-02 DD DD188142A patent/DD124724A5/xx unknown
- 1975-09-02 BR BR7505619*A patent/BR7505619A/pt unknown
- 1975-09-02 CH CH1133775A patent/CH617653A5/de not_active IP Right Cessation
- 1975-09-02 IT IT26821/75A patent/IT1042237B/it active
- 1975-09-02 JP JP50105692A patent/JPS5912093B2/ja not_active Expired
- 1975-09-02 DE DE19752539048 patent/DE2539048A1/de active Granted
- 1975-09-02 FR FR7526844A patent/FR2299302A1/fr active Granted
- 1975-09-03 NL NLAANVRAGE7510373,A patent/NL186314C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU176610B (en) | 1981-03-28 |
| JPS5912093B2 (ja) | 1984-03-21 |
| IT1042237B (it) | 1980-01-30 |
| NL7510373A (nl) | 1976-03-08 |
| DE2539048C2 (xx) | 1988-03-31 |
| DD124724A5 (xx) | 1977-03-09 |
| FR2299302B1 (xx) | 1978-12-29 |
| JPS5170752A (en) | 1976-06-18 |
| IL48032A0 (en) | 1975-11-25 |
| DE2539048A1 (de) | 1976-03-25 |
| BR7505619A (pt) | 1976-08-03 |
| AU8446475A (en) | 1977-03-10 |
| NL186314C (nl) | 1990-11-01 |
| IL48032A (en) | 1979-10-31 |
| FR2299302A1 (fr) | 1976-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |