JPS57163344A - Isomerization of optically active chrysanthemum- monocarboxylic acid ester - Google Patents

Isomerization of optically active chrysanthemum- monocarboxylic acid ester

Info

Publication number
JPS57163344A
JPS57163344A JP4781781A JP4781781A JPS57163344A JP S57163344 A JPS57163344 A JP S57163344A JP 4781781 A JP4781781 A JP 4781781A JP 4781781 A JP4781781 A JP 4781781A JP S57163344 A JPS57163344 A JP S57163344A
Authority
JP
Japan
Prior art keywords
optically active
chrysanthemum
monocarboxylic acid
ester
raw material
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
JP4781781A
Other languages
Japanese (ja)
Other versions
JPS6351137B2 (en
Inventor
Takeo Suzukamo
Masami Fukao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP4781781A priority Critical patent/JPS57163344A/en
Priority to US06/359,319 priority patent/US4473703A/en
Priority to EP82301470A priority patent/EP0062979B1/en
Priority to DE8282301470T priority patent/DE3268358D1/en
Publication of JPS57163344A publication Critical patent/JPS57163344A/en
Publication of JPS6351137B2 publication Critical patent/JPS6351137B2/ja
Granted legal-status Critical Current

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

Abstract

PURPOSE: To prepare the trans-isomer of optically active chrysanthemum-monocarboxylic acid alkyl ester having the same optical rotation as the raw material, useful also as to acid component of pyrethroid having higher insecticidal activity and an optical resolution agent of optically active amine, by reacting an optically active cis-chrysanthemum-monocarboxylic acid alkyl ester with a Lewis acid.
CONSTITUTION: An optically active cis-chrysanthemum-monocarboxylic acid alkyl ester of formulaIor formula II (R is alkyl) or chrysanthemum-monocarboxylic acid alkyl esters containing the above ester, is made to react with a Lewis acid such as boron trifluoride etherate, ferric chloride, etc. at -30W+100°C to transform the steric configuration of the C3-position and to obtain the trans-isomer of formula III or formula IV having the same optical rotation as the ester used as the raw material. The amount of the Lewis acid is preferably 0.01W0.5mol per 1mol of the ester used as the raw material.
COPYRIGHT: (C)1982,JPO&Japio
JP4781781A 1981-03-30 1981-03-30 Isomerization of optically active chrysanthemum- monocarboxylic acid ester Granted JPS57163344A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP4781781A JPS57163344A (en) 1981-03-30 1981-03-30 Isomerization of optically active chrysanthemum- monocarboxylic acid ester
US06/359,319 US4473703A (en) 1981-03-30 1982-03-18 Method of epimerization of alkyl chrysanthemate
EP82301470A EP0062979B1 (en) 1981-03-30 1982-03-22 A method of epimerization of alkyl chrysanthemate
DE8282301470T DE3268358D1 (en) 1981-03-30 1982-03-22 A method of epimerization of alkyl chrysanthemate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4781781A JPS57163344A (en) 1981-03-30 1981-03-30 Isomerization of optically active chrysanthemum- monocarboxylic acid ester

Publications (2)

Publication Number Publication Date
JPS57163344A true JPS57163344A (en) 1982-10-07
JPS6351137B2 JPS6351137B2 (en) 1988-10-13

Family

ID=12785901

Family Applications (1)

Application Number Title Priority Date Filing Date
JP4781781A Granted JPS57163344A (en) 1981-03-30 1981-03-30 Isomerization of optically active chrysanthemum- monocarboxylic acid ester

Country Status (1)

Country Link
JP (1) JPS57163344A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57176930A (en) * 1981-04-24 1982-10-30 Sumitomo Chem Co Ltd Preparation of trans-chrysanthemumic acid alkyl ester
JP2003002866A (en) * 2001-06-20 2003-01-08 Sumitomo Chem Co Ltd Method for producing trans-cyclopropane carboxylic esters each substituted with vinyl group

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57176930A (en) * 1981-04-24 1982-10-30 Sumitomo Chem Co Ltd Preparation of trans-chrysanthemumic acid alkyl ester
JPH0312050B2 (en) * 1981-04-24 1991-02-19 Sumitomo Chemical Co
JP2003002866A (en) * 2001-06-20 2003-01-08 Sumitomo Chem Co Ltd Method for producing trans-cyclopropane carboxylic esters each substituted with vinyl group

Also Published As

Publication number Publication date
JPS6351137B2 (en) 1988-10-13

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