CS198298B2 - Method of producing substituted benzylesters of vinyl cyclopropane carboxylic acids - Google Patents

Method of producing substituted benzylesters of vinyl cyclopropane carboxylic acids Download PDF

Info

Publication number: CS198298B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; reaction; halogen; acid; esters
Prior art date: 1977-05-11

Application number

CS782980A

Other languages

Czech (cs)

English (en)

Inventor

Klaus Naumann

Ruediger Schubert

Thomas Schmidt

Original Assignee

Bayer Ag

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.)

1977-05-11

Filing date

1978-05-10

Publication date

1980-05-30

1978-05-10 Application filed by Bayer Ag filed Critical Bayer Ag

1980-05-30 Publication of CS198298B2 publication Critical patent/CS198298B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 10
PDOBSLHNWIVQJX-UHFFFAOYSA-N 1-ethenylcyclopropane-1-carboxylic acid Chemical class OC(=O)C1(C=C)CC1 PDOBSLHNWIVQJX-UHFFFAOYSA-N 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 16
150000002148 esters Chemical class 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 8
238000000746 purification Methods 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 4
229940073608 benzyl chloride Drugs 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
239000003513 alkali Substances 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract 4
238000006243 chemical reaction Methods 0.000 claims description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
238000007127 saponification reaction Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
239000004567 concrete Substances 0.000 claims 1
-1 vinyl-cyclopropanecarboxylic acid ester Chemical class 0.000 abstract description 14
238000005660 chlorination reaction Methods 0.000 abstract description 13
238000002360 preparation method Methods 0.000 abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
125000004432 carbon atom Chemical group C* 0.000 abstract 3
125000005843 halogen group Chemical group 0.000 abstract 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
159000000011 group IA salts Chemical group 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
239000002253 acid Substances 0.000 description 16
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000012071 phase Substances 0.000 description 9
UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
150000007513 acids Chemical class 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
239000007789 gas Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
150000005524 benzylchlorides Chemical class 0.000 description 4
238000004821 distillation Methods 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-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
LLFHCOGPDCJMKY-UHFFFAOYSA-N 3,3,4-trimethylpent-1-ene Chemical group CC(C)C(C)(C)C=C LLFHCOGPDCJMKY-UHFFFAOYSA-N 0.000 description 1
TTZXIWBOKOZOPL-UHFFFAOYSA-N 3-phenoxybenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 TTZXIWBOKOZOPL-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
JJBXIMAIIIEIIS-UHFFFAOYSA-N [Li].[CH](Oc1ccccc1)c1ccccc1 Chemical compound [Li].[CH](Oc1ccccc1)c1ccccc1 JJBXIMAIIIEIIS-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
XYNZKHQSHVOGHB-UHFFFAOYSA-N copper(3+) Chemical compound [Cu+3] XYNZKHQSHVOGHB-UHFFFAOYSA-N 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical class C=CC1CC1 YIWFBNMYFYINAD-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
238000001914 filtration Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
UWAAFUVSRWSVSK-UHFFFAOYSA-N phenoxybenzene;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OC1=CC=CC=C1 UWAAFUVSRWSVSK-UHFFFAOYSA-N 0.000 description 1
BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000004513 sizing Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS782980A 1977-05-11 1978-05-10 Method of producing substituted benzylesters of vinyl cyclopropane carboxylic acids CS198298B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772721185 DE2721185A1 (de)	1977-05-11	1977-05-11	Verfahren zur herstellung von substituierten vinylcyclopropancarbonsaeurebenzylestern

Publications (1)

Publication Number	Publication Date
CS198298B2 true CS198298B2 (en)	1980-05-30

Family

ID=6008622

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS782980A CS198298B2 (en)	1977-05-11	1978-05-10	Method of producing substituted benzylesters of vinyl cyclopropane carboxylic acids

Country Status (17)

Country	Link
US (1)	US4256907A (de)
JP (1)	JPS53141247A (de)
AT (1)	AT355005B (de)
BE (1)	BE866909A (de)
BR (1)	BR7802936A (de)
CS (1)	CS198298B2 (de)
DD (1)	DD138898A5 (de)
DE (1)	DE2721185A1 (de)
DK (1)	DK204878A (de)
FR (1)	FR2390417A1 (de)
GB (1)	GB1584526A (de)
HU (1)	HU175042B (de)
IL (1)	IL54665A (de)
IT (1)	IT7823198A0 (de)
NL (1)	NL7804910A (de)
PL (1)	PL110204B1 (de)
SU (1)	SU725553A3 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2840992A1 (de) *	1978-09-21	1980-05-29	Bayer Ag	Mittel gegen bodeninsekten
CA1150300A (en) *	1978-10-13	1983-07-19	Robert J.G. Searle	2,6-dihalobenzyl esters and their use as pesticides
DE3005722A1 (de) *	1980-02-15	1981-08-20	Bayer Ag, 5090 Leverkusen	Trifluormethylbenzylester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln
DE2939913A1 (de) *	1979-10-02	1981-04-30	Bayer Ag, 5090 Leverkusen	3-(2,3-dichlor-3,3-difluor-prop-1-en-1-yl)-2,2-dimethyl-cyclopropancarbonsaeure-fluor-benzylester, verfahren zu ihrer herstellung sowie ihre verwendung in schaedlingsbekaempfungsmitteln
DE3065914D1 (en) *	1979-12-21	1984-01-19	Ici Plc	Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols
NL8006593A (nl) *	1979-12-21	1981-07-16	Ciba Geigy	Cyclopropaanderivaten, werkwijzen ter bereiding ervan en hun toepassing.
US4370346A (en)	1979-12-21	1983-01-25	Imperial Chemical Industries Plc	Halogenated esters
DE3705224A1 (de) *	1987-02-19	1988-09-01	Bayer Ag	(+)1r-trans-2,2-dimethyl-3-(2,2-dichlorvinyl) -cyclopropancarbonsaeure-2,3,5,6- tetrafluorbenzylester
US5238957A (en) *	1988-07-07	1993-08-24	Presidenza Del Consiglio Dei Ministri-Uffico Del Ministro Per Il Coordinamento Delle Iniziative Per La Ricerca Scientifica E Tecnologica	Esters of 2,2-dimethyl-cyclopropane-carboxylic acid
MX2020005099A (es) *	2017-11-16	2020-08-13	Lg Chemical Ltd	Metodo de produccion de un compuesto intermedio para sintetizar un medicamento.
KR102184129B1 (ko) *	2017-11-16	2020-11-27	주식회사 엘지화학	의약품 합성용 중간체 화합물의 제조 방법

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB633435A (en) *	1946-06-22	1949-12-19	Monsanto Chemicals	Improvements in or relating to process for producing paraacetylbenzyl acetate, para-(alpha-hydroxyethyl) benzyl acetate and para-(alpha-acetoxyethyl) benzyl acetate
GB1102838A (en) *	1965-02-19	1968-02-14	Sumitomo Chemical Co	Cyclopropanecarboxylic acid esters, methods of making them and insecticidal compositions including them
US3850977A (en) *	1968-06-06	1974-11-26	Sumitomo Chemical Co	3-substituted-benzyl cyclopropane-carboxylates
US3663591A (en) *	1968-12-09	1972-05-16	Hoffmann La Roche	Chrysanthemic acid esters
US3666789A (en) *	1969-05-21	1972-05-30	Sumitomo Chemical Co	Cyclopropanecarboxylic acid esters
JPS4831891B1 (de) *	1970-03-19	1973-10-02
JPS49489B1 (de) *	1970-06-13	1974-01-08
US4024163A (en) *	1972-05-25	1977-05-17	National Research Development Corporation	Insecticides
GB1438129A (de) *	1973-12-21	1976-06-03
GB1533856A (en) *	1975-03-24	1978-11-29	Shell Int Research	Process for the preparation of meta-aryloxy benzyl bromides
GB1559799A (en) *	1975-11-12	1980-01-30	Shell Int Research	Process for preparing substituted benzylesters

1977
- 1977-05-11 DE DE19772721185 patent/DE2721185A1/de not_active Withdrawn
1978
- 1978-04-24 US US05/899,664 patent/US4256907A/en not_active Expired - Lifetime
- 1978-05-04 SU SU782610503A patent/SU725553A3/ru active
- 1978-05-06 PL PL1978206644A patent/PL110204B1/pl unknown
- 1978-05-08 NL NL7804910A patent/NL7804910A/xx not_active Application Discontinuation
- 1978-05-08 IL IL54665A patent/IL54665A/xx unknown
- 1978-05-08 GB GB18249/78A patent/GB1584526A/en not_active Expired
- 1978-05-09 DD DD78205274A patent/DD138898A5/de unknown
- 1978-05-09 AT AT336078A patent/AT355005B/de not_active IP Right Cessation
- 1978-05-09 IT IT7823198A patent/IT7823198A0/it unknown
- 1978-05-10 BE BE187558A patent/BE866909A/xx unknown
- 1978-05-10 DK DK204878A patent/DK204878A/da unknown
- 1978-05-10 HU HU78BA3652A patent/HU175042B/hu unknown
- 1978-05-10 JP JP5456478A patent/JPS53141247A/ja active Pending
- 1978-05-10 CS CS782980A patent/CS198298B2/cs unknown
- 1978-05-10 BR BR7802936A patent/BR7802936A/pt unknown
- 1978-05-10 FR FR7813914A patent/FR2390417A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
FR2390417A1 (fr)	1978-12-08
DK204878A (da)	1978-11-12
US4256907A (en)	1981-03-17
PL110204B1 (en)	1980-07-31
IT7823198A0 (it)	1978-05-09
AT355005B (de)	1980-02-11
BR7802936A (pt)	1979-01-02
JPS53141247A (en)	1978-12-08
PL206644A1 (pl)	1979-04-23
DD138898A5 (de)	1979-11-28
DE2721185A1 (de)	1978-11-16
SU725553A1 (ru)	1980-03-30
IL54665A0 (en)	1978-07-31
IL54665A (en)	1981-07-31
HU175042B (hu)	1980-05-28
GB1584526A (en)	1981-02-11
SU725553A3 (en)	1980-03-30
BE866909A (fr)	1978-11-10
NL7804910A (nl)	1978-11-14
ATA336078A (de)	1979-07-15

Publication	Publication Date	Title
CS198298B2 (en)	1980-05-30	Method of producing substituted benzylesters of vinyl cyclopropane carboxylic acids
JP2693615B2 (ja)	1997-12-24	１‐ハロ‐４，６，１０‐ヘキサデカトリエン化合物およびその製造方法
JPH03184938A (ja)	1991-08-12	エチレン性ケトンの製造方法
JPH07300445A (ja)	1995-11-14	４−ハロ−２′−ニトロブチロフエノン化合物の製造方法
US4210611A (en)	1980-07-01	Halogenated hydrocarbons, useful as insecticide intermediates, and methods for their preparation
JP2682687B2 (ja)	1997-11-26	新規チオフエン化合物およびそれらの製造
US4442301A (en)	1984-04-10	Process for stereoselectively synthesizing cyclopropane carboxylates
ZA200210300B (en)	2004-09-06	Process for the preparation of trifluoroethoxy-substituted benzoic acids.
JP7825591B2 (ja)	2026-03-06	１－ハロ－２，６，１４－トリメチルオクタデカン化合物、並びにそれを用いた５，１３，１７－トリメチルアルカン化合物の製造方法
JPS647065B2 (de)	1989-02-07
EP0473110A1 (de)	1992-03-04	Verfahren zur Herstellung isoprenoider Cyclopropan-1,1-dicarboxylate und ihrer Derivate und neue Zwischenprodukte
JPH05286902A (ja)	1993-11-02	α−クロロ−β−ケトエステル誘導体の製造方法
JP3823385B2 (ja)	2006-09-20	２，４，５−トリフルオロ−３−ヨ−ド安息香酸およびそのエステル類の製造方法
JP2021518350A (ja)	2021-08-02	２−メチル−４−（２，６，６−トリメチル−１−シクロヘキセン−１−イル）−２−ブテナールを生成するためのプロセス
EP0022607B1 (de)	1983-01-12	Verfahren zur Herstellung halogenierter Kohlenwasserstoffe
US4092482A (en)	1978-05-30	Process for preparing 6,6,6-trihalo-3,3-dimethyl-4-hexenoates
JPS59163345A (ja)	1984-09-14	α−アリ−ルアルカン酸エステル類の製造法
JPS6232188B2 (de)	1987-07-13
JP2743198B2 (ja)	1998-04-22	シクロペンタン類
JPH0572895B2 (de)	1993-10-13
JPH0372054B2 (de)	1991-11-15
GB2155008A (en)	1985-09-18	One solvent process for preparation of esters of 3,5-dibromo-4-hydroxybenzonitrile
US4667050A (en)	1987-05-19	Preparation of pyrethroid precursors
JPH075515B2 (ja)	1995-01-25	２−シクロペンテノン誘導体の製法
JP2581186B2 (ja)	1997-02-12	４−置換−２−シクロペンテノンエステル誘導体の製造法