合成香料环己氧基乙酸烯丙酯和异戊氧基乙酸烯丙酯的新方法

A novel process for synthesis of flavor allyl cyclohexoxyacetate and allyl amyl glycolate

提供了一种更温和的方法代替Williamson反应制备香料环己氧基乙酸烯丙酯和异戊氧基乙酸烯丙酯。采用重氮乙酸乙酯(EDA)分别与环己醇和异戊醇在二水杨醛铜催化作用下进行O—H插入反应合成了上述香料的前体化合物环己氧基乙酸乙酯和异戊氧基乙酸乙酯,研究了催化剂、反应温度和物料比例对插入反应收率的影响,在优化的反应条件下二者的反应收率分别为83%和79%。

This study provided a more facile process in place of Williamson reaction for the synthesis of flavor allyl cyclohexoxyacetate and allyl amyl glyeolate, Ethyl diazoncetate （EDA） undergoes a facile bis （salicylaldehydato） copper carbenoid mediated O-H insertion reaction with cyclohexanol and isonmyl alcohol to afford ethyl 2-cyclohexyloxry-acetate （ Ⅰ ） and ethyl 2-（3-methyl-2-butyloxy）-acetate （ Ⅱ ）. These compounds were used as synthetic precursor for title compounds. The effects of catalyst, reaction temperature as well as the ratio of alcohol and EDA on insertion yield were discussed. Under optimized reaction conditions the compounds （ Ⅰ ） and （ Ⅱ ） were respectively obtained in an 83% and a 79% reaction yield.