A new method for synthesis of 2,4,6-trimethoxydeoxybenzoin

2,4,6-trimethoxydeoxybenzoin was prepared through Houben-Hoesch reaction from 1,3,5-trimethoxybenzene and 2-phenylacetonitrile.Toluene was used as solvent instead of highly volatile and particularly hazardous diethyl ether.The product was characterized by 1HNMR and MS.Because of the protective effect of ether bond,the reactivity of hydroxy group was reduced and the side reactions were inhibited.With this improved synthetic method,the yield of Houben-Hoesch reaction reached up to 81.3%.In this work,the effects of the ratio of raw materials(1,3,5-trimethoxybenzene∶2-phenylacetonitrile),reaction time and the amount of zinc chloride on the yield were investigated.Optimization of reaction conditions were as follows: the ratio of raw materials(1,3,5-trimethoxybenzene∶2-phenylacetonitrile) was 1.2∶1,reaction time 28 h and the ratio of zinc chloride and 2-phenylacetonitrile 0.3∶1.