Study On The Synthesis Of Aromatic Compounds Containing Carboxymethyl Sulfonyl Function

Aromatic compound containing the carboxymethyl sulfonyl function is a kind of very important organic synthetic intermediates. It not only can be used to synthesize Mesotrion applied in the field of pesticide, but also can be used to synthesize a,(3-unsaturated sulphone compounds and thiamphenicol which applied in medicine. Based on its wide range of applications, it is significant to investigate the synthesis of aromatic compound containing carboxymethyl sulfonyl function in high. The synthesis of carboxymethylsulfonyl aromatic compounds which are reported in the literature has some problems such as low yield, complicated process and harsh reaction conditions, so we need to find a relatively mild synthetic route with available raw materials, simple reaction process and higher yield.This paper has proposed a synthetic route for carboxymethylsulfonyl aromatic compounds—p-toluenesulfonylacetic acid and benzenesulfonylacetic acid, which involves using p-toluene and benzene as the starting materials, through chlorosulfonation, reduction and carboxymethylation. In addition, this paper explore the synthesis of N-carboxylmethyl sulfonylpropyl aniline with the same route.The second important content of this paper deeply investigated the reaction from p-toluenesulfonyl chloride to p-toluenesulfonylacetic acid, which taked the method of one-pot with reduction and carboxymethylation. This paper optimizes the reaction condition:using sodium sulfite as the reductant, the reduction condition of p-toluenesulfonyl chloride:acid scavenger:10%sodium hydroxide solution; pH=8; reduction reaction temperature70℃, reaction time3h, n (p-Toluene sulfonyl chloride):n (sodium sulfite)=1:1.1. After the completion of the reduction reaction, sodium chloroacetate was joined directly in the reaction system on the reaction of carboxy methyl. Using sodium chloroacetate as reagents for carboxy methylation, reacting4h and then acidificating product with hydrochloric acid, the yield is up to97.9%.