2-对乙氧基苯基丙烯酸乙酯的合成研究  

Synthesis of Ethyl-2-(p-ethoxyphenyl) Propenoate

作　　者：孙娜波[1] 沈德隆[1] 谭成侠[1] 翁建全[1] 

机构地区：[1]浙江工业大学化学工程与材料学院,浙江杭州310032

出　　处：《高校化学工程学报》2007年第2期361-364,共4页Journal of Chemical Engineering of Chinese Universities

摘　　要：2-对乙氧基苯基丙烯酸乙酯是合成乙氰菊酯的重要中间体。设计了一条以苯乙醚为起始原料,经过Friedel-Crafts反应、WittigG反应合成2-对乙氧基苯基丙烯酸乙酯的新路线。在反应中考察了溶剂、投料比(摩尔比)对反应收率的影响,得到了较佳的反应条件。在Friedel-Crafts反应中,以二氯甲烷为溶剂,苯乙醚、三氯化铝、草酰氯单乙酯的投料比(摩尔比)为1:2.5:1.2,反应收率达76.5%,含量在92.0%以上;在WittigG反应中,以四氢呋喃为溶剂,甲基三苯基溴化膦与α-羰基-对乙氧基-苯乙酸乙酯的投料比(摩尔比)为1:1,反应收率达83.0%,含量为93.8%。两步反应总收率为63.8%。此合成路线简单,反应条件温和,原料价廉易得。中间产物和产品结构经1H-NMR、MS、IR表征。Ethyl-2-（p-ethoxyphenyl） propenoate is the important intermediate for synthesizing cycloprothrin, an ideal substituent for those highly poisonous pesticides. A new synthesizing route for ethyl-2-（p -ethoxyphenyl） propenoate preparation was proposed, in which, the ethyl-2-（p-ethoxyphenyl） propenoate was synthesized from phenetole via Friedel-Crafts reaction and Wittig G reaction. The effects of the solvents and molar ratio of reactants on the reactions were investigated, and the suitable reaction conditions were obtained as follows. In Friedel-Crafts reaction, the suitable solvent is dichloromethane, the molar ratio between phenetole, aluminium trichloride and ethyl oxaloyl chloride is 1：2.5：1.2, and in this reaction, the yield and the content of the product can reach 76.5% and above 92.0%, respectively. In Wittig G reaction, the solvent is tetrahydrofuran, the molar ratio between methyltriphenylphosphonium bromide and α-oxo-4-ethoxyphenylacetic acid ethyl ester is 1：1, and the yield and the content of the product in this reaction can reach 83.0% and 93.8%, respectively. The overall yield of above two reactions is about 63.8%, and the structures of the products for each reaction were confirmed by ^1H-NMR, MS and IR. The proposed synthesizing route is simple, the reaction conditions are mild and the raw materials are cheap and easy to obtain.

关 键 词：苯乙醚 α-羰基-对乙氧基-苯乙酸乙酯 2-对乙氧基苯基丙烯酸乙酯 合成 

分 类 号：TQ245.24[化学工程—有机化工]