相转移催化法合成3-巯基丙酸(4-乙烯基苯基)甲酯  

Synthesis of 4-vinylbenzyl-3-mercaptopropionate by phase transfer catalysis

作　　者：郑蕾[1] 黄文艳[1] 薛小强[1] 蒋必彪[1] 

机构地区：[1]常州大学材料科学与工程学院,江苏常州213164

出　　处：《化学试剂》2012年第8期746-749,共4页Chemical Reagents

基　　金：国家自然科学基金资助项目(21174020)

摘　　要：对氯甲基苯乙烯(CMS)在相转移催化剂(PTC)催化下,与3-巯基丙酸钾进行亲核取代反应,制备了标题化合物。研究了溶剂、催化剂及反应温度对反应的影响,实验结果表明:以二甲苯为溶剂,以三乙胺为相转移催化剂,催化剂与CMS的物质的量之比为1∶10,80℃下反应8 h,3-巯基丙酸(4-乙烯基苯基)甲酯的产率达60.7%,HPLC分析得到产物纯度>98%,1HNMR分析确证了产物结构。4-Vinylbenzyl-3-mercaptopropionate was synthe- sized by nucleophilic substitution reaction of 4-vinylbenzyl chloride （CMS） and potassium 3-mercaptopropionic acid po- tassium salt,using phase transfer catalyst （ PTC）. The purity and structure of the products were characterized using HPLC and ~ HNMR. The effects of the solvent, catalyst and tempera- ture on the structure and yield of products in the reaction were studied. The results showed that 4-vinylbenzyl-3-mereaptopro- pionate （MPVBMA） with polymerizable double bond and chain transfer sulfhydry] group was prepared using non-polar solvent such as benzene, toluene or xylene, while 3-（ （4-vinyl- benzyl） thio） propanoate was obtained using polar solvent as dimethyl sulfoxide （DMSO）, N, N-dimethylformamide （DMF） or acetone. The highest yield of MPVBMA was obtained at 80℃ using xylene as the solvent and triethylamine as the PTC under the condition of n （CMS） ： n （ HSCH2 CH2 COOK ） ： n（TEA） =1：1.5：0.1.

关 键 词：对氯甲基苯乙烯 3-巯基丙酸钾 相转移催化 三乙胺 

分 类 号：O625.72[理学—有机化学]