BE431768A - - Google Patents

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Publication number: BE431768A
Authority: BE; Belgium
Prior art keywords: hydroxyl groups; page; letter; compounds; line
Prior art date

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Publication of BE431768A publication Critical patent/BE431768A/fr

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125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
238000000034 method Methods 0.000 claims description 11
230000003647 oxidation Effects 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
239000007800 oxidant agent Substances 0.000 claims description 8
238000007792 addition Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
230000000875 corresponding Effects 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000002015 acyclic group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
150000001875 compounds Chemical class 0.000 description 14
239000000203 mixture Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
238000002844 melting Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
229960000583 Acetic Acid Drugs 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
VUVGYHUDAICLFK-UHFFFAOYSA-N Perosmic oxide Chemical compound O=[Os](=O)(=O)=O VUVGYHUDAICLFK-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
125000004430 oxygen atoms Chemical group O* 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
210000004404 Adrenal Cortex Anatomy 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
229940088597 Hormone Drugs 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QCDFBFJGMNKBDO-UHFFFAOYSA-N Quinoform Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atoms Chemical group C* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
-1 halogen hydride Chemical class 0.000 description 2
239000005556 hormone Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
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 2
GRXPVLPQNMUNNX-MHJRRCNVSA-N (8R,9R,10S,13S,14S)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-hexadecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N (8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-Dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
241000589220 Acetobacter Species 0.000 description 1
210000004100 Adrenal Glands Anatomy 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
CHNXZKVNWQUJIB-CEGNMAFCSA-N Ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 1
229960000445 Ethisterone Drugs 0.000 description 1
LMCPVTRIVCJCKI-XGDSOOHZSA-N O[C@]1(C(=C(O)O)O)CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C Chemical compound O[C@]1(C(=C(O)O)O)CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C LMCPVTRIVCJCKI-XGDSOOHZSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
UUJASHLQKQMDHX-UHFFFAOYSA-L S(=O)([O-])[O-].[Os+4].[Na+] Chemical compound S(=O)([O-])[O-].[Os+4].[Na+] UUJASHLQKQMDHX-UHFFFAOYSA-L 0.000 description 1
229940100996 SODIUM BISULFATE Drugs 0.000 description 1
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M Sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N Triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
FSNPVPKZMCRGTL-UHFFFAOYSA-N [Al].CC=C Chemical group [Al].CC=C FSNPVPKZMCRGTL-UHFFFAOYSA-N 0.000 description 1
XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 description 1
239000000061 acid fraction Substances 0.000 description 1
230000001919 adrenal Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
230000001684 chronic Effects 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000005712 crystallization Effects 0.000 description 1
238000007256 debromination reaction Methods 0.000 description 1
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000005530 etching Methods 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
150000003130 pregnenes Chemical class 0.000 description 1
125000000075 primary alcohol group Chemical group 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000003198 secondary alcohol group Chemical group 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
230000001131 transforming Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE431768D BE431768A (fi)

Publications (1)

Publication Number	Publication Date
BE431768A true BE431768A (fi)

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ID=91496

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE431768D BE431768A (fi)

Country Status (1)

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BE (1)	BE431768A (fi)

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- BE BE431768D patent/BE431768A/fr unknown

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