CH634035A5 - Derivatives of cyclopropane and processes for preparing them - Google Patents

Derivatives of cyclopropane and processes for preparing them Download PDF

Info

Publication number: CH634035A5
Authority: CH; Switzerland
Prior art keywords: acid; zinc; formula; compounds; ppm
Prior art date: 1977-01-26

Application number

CH75178A

Other languages

German (de)

English (en)

Inventor

Pieter Adriaan Verbrugge

Petrus Antonius Kramer

Original Assignee

Shell Int Research

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-01-26

Filing date

1978-01-24

Publication date

1983-01-14

1978-01-24 Application filed by Shell Int Research filed Critical Shell Int Research

1983-01-14 Publication of CH634035A5 publication Critical patent/CH634035A5/de

Links

238000000034 method Methods 0.000 title claims description 15
125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 title 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 53
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 44
239000011701 zinc Substances 0.000 claims description 31
229910052725 zinc Inorganic materials 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000005907 alkyl ester group Chemical group 0.000 claims description 9
150000003863 ammonium salts Chemical class 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000003857 carboxamides Chemical class 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 5
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
238000005695 dehalogenation reaction Methods 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 claims description 2
229910000083 tin tetrahydride Inorganic materials 0.000 claims description 2
229960000583 acetic acid Drugs 0.000 claims 2
239000003513 alkali Substances 0.000 claims 1
239000012362 glacial acetic acid Substances 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
YUBCVMNXGPVXID-UHFFFAOYSA-N 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(Cl)Cl YUBCVMNXGPVXID-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 8
238000010992 reflux Methods 0.000 description 8
GHXJAGHRKSJMPQ-UHFFFAOYSA-N 3-chloro-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(Cl)C1C(O)=O GHXJAGHRKSJMPQ-UHFFFAOYSA-N 0.000 description 6
101000716807 Arabidopsis thaliana Protein SCO1 homolog 1, mitochondrial Proteins 0.000 description 6
101001076715 Homo sapiens RNA-binding protein 39 Proteins 0.000 description 6
102100023361 SAP domain-containing ribonucleoprotein Human genes 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000006298 dechlorination reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
230000009102 absorption Effects 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
150000001942 cyclopropanes Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
LNEFGAYKTMMXDW-UHFFFAOYSA-N tert-butyl 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1C(C)(C)C1(Cl)Cl LNEFGAYKTMMXDW-UHFFFAOYSA-N 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
ZJAJKMDQAODLNY-UHFFFAOYSA-N methyl 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C)(C)C1(Cl)Cl ZJAJKMDQAODLNY-UHFFFAOYSA-N 0.000 description 2
VPQWGHHXCIHSCW-UHFFFAOYSA-N methyl 3-chloro-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(Cl)C1(C)C VPQWGHHXCIHSCW-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
QCRGTFXKYABKHU-UHFFFAOYSA-N tert-butyl 3-chloro-2,2-dimethylcyclopropane-1-carboxylate Chemical compound ClC1C(C1C(=O)OC(C)(C)C)(C)C QCRGTFXKYABKHU-UHFFFAOYSA-N 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
ZLIUAIJHSXKIDP-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].[Zn].CC(O)=O ZLIUAIJHSXKIDP-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
-1 tetramethylene silane Chemical compound 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1

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

CH75178A 1977-01-26 1978-01-24 Derivatives of cyclopropane and processes for preparing them CH634035A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3164/77A GB1594224A (en)	1977-01-26	1977-01-26	Preparation of cyclopropane derivatives

Publications (1)

Publication Number	Publication Date
CH634035A5 true CH634035A5 (en)	1983-01-14

Family

ID=9753142

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH75178A CH634035A5 (en)	1977-01-26	1978-01-24	Derivatives of cyclopropane and processes for preparing them

Country Status (11)

Country	Link
JP (1)	JPS5392743A (es)
BE (1)	BE863272A (es)
BR (1)	BR7800411A (es)
CA (1)	CA1121831A (es)
CH (1)	CH634035A5 (es)
DE (1)	DE2802967A1 (es)
FR (1)	FR2378740A1 (es)
GB (1)	GB1594224A (es)
IT (1)	IT7819574A0 (es)
MX (1)	MX4672E (es)
NL (1)	NL7800811A (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3026093C2 (de) *	1980-07-10	1983-02-10	Degussa Ag, 6000 Frankfurt	1-Methyl-2-chlorcyclopropancarbonsäure und deren verzweigte und unverzweigte C↓1↓ bis C↓6↓-Alkylester, sowie Verfahren zu deren Herstellung
CN1304356C (zh) *	2003-01-07	2007-03-14	第一制药株式会社	还原脱卤方法

1977
- 1977-01-26 GB GB3164/77A patent/GB1594224A/en not_active Expired
1978
- 1978-01-04 CA CA000294304A patent/CA1121831A/en not_active Expired
- 1978-01-24 BR BR7800411A patent/BR7800411A/pt unknown
- 1978-01-24 IT IT7819574A patent/IT7819574A0/it unknown
- 1978-01-24 JP JP588578A patent/JPS5392743A/ja active Pending
- 1978-01-24 BE BE184604A patent/BE863272A/xx not_active IP Right Cessation
- 1978-01-24 DE DE19782802967 patent/DE2802967A1/de not_active Withdrawn
- 1978-01-24 NL NL7800811A patent/NL7800811A/xx not_active Application Discontinuation
- 1978-01-24 FR FR7801895A patent/FR2378740A1/fr active Granted
- 1978-01-24 MX MX678678U patent/MX4672E/es unknown
- 1978-01-24 CH CH75178A patent/CH634035A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2378740A1 (fr)	1978-08-25
NL7800811A (nl)	1978-07-28
FR2378740B1 (es)	1981-08-21
BE863272A (fr)	1978-07-24
GB1594224A (en)	1981-07-30
DE2802967A1 (de)	1978-07-27
CA1121831A (en)	1982-04-13
JPS5392743A (en)	1978-08-15
MX4672E (es)	1982-07-23
BR7800411A (pt)	1978-08-22
IT7819574A0 (it)	1978-01-24

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DE2437882B2 (de)	1977-08-25	Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols
CH634035A5 (en)	1983-01-14	Derivatives of cyclopropane and processes for preparing them
DE1668516A1 (de)	1971-09-02	Bifunktionelle Cyclohexenylverbindungen und deren Herstellung
DE2920591C2 (es)	1989-11-16
DE852851C (de)	1952-10-20	Verfahren zur Herstellung von Alkylestern ª‡, ª‰-ungesaettigter Monocarbonsaeuren
EP0136566B1 (de)	1987-04-01	Verfahren zur Herstellung von 3,4-Dichlorbenzotrihalogeniden
EP0048370B1 (de)	1983-05-18	Verfahren zur Herstellung von trans-3-(Z-2-Chlor-2-aryl-vinyl)-2,2-dimethyl-cyclopropan-1-carbon-säure-derivaten, neue Zwischenprodukte hierfür, Verfahren zu deren Herstellung und Verwendung von Zwischenprodukten in Schädlingsbekämpfungsmitteln
DE2729911A1 (de)	1978-01-12	Verfahren zur herstellung von alpha-chloralkanoylchloriden
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EP0002206A1 (de)	1979-06-13	Halogenierte Buttersäurechloride, Verfahren zu deren Herstellung und ihre Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln
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DE69005000T2 (de)	1994-04-28	Verfahren zur Herstellung von Acrylsäurechlorid.
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DE2247765B2 (de)	1974-09-26	Verfahren zur Herstellung von Monohalogenacy !halogeniden
DE69023246T2 (de)	1996-05-02	Verfahren zur herstellung von optisch aktiven oder racemischen cyclopropancarbonsäurechloriden.
DE2008115C3 (de)	1978-09-07	Verfahren zur Herstellung von Naralkylsubstituierten N-Acylcarbamidsäurehalogeniden
DE1468142C (es)

Legal Events

Date	Code	Title	Description
1985-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased