Patent ID: 9079848
Filing Date: 2015-07-14
Classification: C07C

Abstract:
1. A method for preparing an (3E)-3-alkenyl acetate comprising at least the steps of: reacting 4-formyl-(3E)-3-butenyl methoxymethyl ether with a reductant to obtain 5-hydroxy-(3E)-3-pentenyl methoxymethyl ether; reacting the 5-hydroxy-(3E)-3-pentenyl methoxymethyl ether with an acetylating agent to obtain 5-acetoxy-(3E)-3-pentenyl methoxymethyl ether; subjecting the 5-acetoxy-(3E)-3-pentenyl methoxymethyl ether to a coupling reaction at a temperature of from 0 to 20° C. with a Grignard reagent, wherein the Grignard reagent is (Z3,Z6)-3,6-nonadienylmagnesium halide or (Z3)-3-nonenylmagnesium halide, so that the 5-acetoxy group is replaced by either (Z3,Z6)-3,6-nonadienyl or (Z3)-3-nonenyl to obtain (3E)-3-alkenyl methoxymethyl ether; treating the (3E)-3-alkenyl methoxymethyl ether with an acid to obtain (3E)-3-alkenyl alcohol; and reacting the (3E)-3-alkenyl alcohol with an acetylating agent to obtain the (3E)-3-alkenyl acetate, wherein the reductant is sodium borohydride and the (3E)-3-alkenyl acetate is (3E,Z8,Z11)-3,8,11-tetradecatrienyl acetate or (3E,ZS)-3,8-tetradecadienyl —acetate.