Weng Jianquan
2007
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Journal
Journal of Chemical Engineering of Chinese Universities
Abstract
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.