Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1989-05-04
1990-03-27
Evans, J. E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560254, 568813, 568874, 568876, 5689095, 568851, 568841, 556470, C07C 2940, C07C 33025, C07C 3320, C07C 6708
Patent
active
049122533
ABSTRACT:
An efficient method is proposed for the synthesis of an unsaturated alcohol of the general formula R--CH.dbd.CH(CH.sub.2).sub.n+1 OH, in which R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms and the subscript n is an integer in the range from 3 to 10, in which an acetate of the formula R--CH.dbd.CHCH.sub.2 OCOCH.sub.3 is subjected to a coupling reaction with a Grignard reagent of the formula X.sup.1 Mg(CH.sub.2).sub.n OMgX.sup.2, in which X.sup.1 and X.sup.2 are each a halogen atom, and then the reaction product is hydrolyzed. When the reaction product of the coupling reaction is reacted with acetic anhydride instead of hydrolysis, the corresponding acetate can readily be obtained. These unsaturated alcohols and acetates form a class of important biologically active compounds or intermediates thereof including sex pheromone compounds of insects.
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Fukumoto Takehiko
Yamamoto Akira
Evans J. E.
Shin-Etsu Chemical Co. , Ltd.
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