L-薄荷基氯甲烷的合成研究  

The Synthesis of L-Menthylchloromethane

作　　者：阳年发[1] 张祚[1] 欧阳歆[1] 

机构地区：[1]环境友好化学与应用教育部重点实验室湘潭大学化学学院,湖南湘潭411105

出　　处：《湘潭大学自然科学学报》2009年第3期96-100,共5页Natural Science Journal of Xiangtan University

基　　金：国家自然科学基金资助项目(20772102);教育部博士点专项科研基金资助项目(20060530002)

摘　　要：从L-薄荷醇出发经过氯代反应、羧酸化反应、还原反应、氯代反应合成了立体构型保持的L-薄荷基氯甲烷.同时,对各步反应的实验条件进行了优化,找到了较好的合成条件,并用1H NMR和13C NMR对各步产物进行了表征.合成薄荷基氯甲烷较好的条件是:在-78℃和搅拌下往薄荷基氯化镁溶液中通入二氧化碳,得到薄荷基甲酸;采用氢化铝锂作还原剂,将所得的薄荷基甲酸在无水四氢呋喃中回流还原1 h,得到薄荷基甲醇;利用所得的薄荷基甲醇制成二甲基甲酰胺溶液,该溶液在35℃下与1.5倍的二氯亚砜反应,并在反应过程中用水泵减压抽出生成的氯化氢,最后得到薄荷基氯甲烷.以薄荷基氯计算,薄荷基氯甲烷的总产率为25.2%.L- menthylchloromethane was synthesized from L- menthyl via chlorination, carboxylation, reduction and chlorination. The suitable reaction conditions were obtained and structures of the products were identified by 1HNMR and 13HNMR. The appropriate conditions for the synthesis of menthylcblorometh- ane are following： the carbon dioxide was bubbled into the menthylmagnesuim chloride solution in tetrahydrofuran at 78℃ with stir to afford menthylformic acid, the menthylformic acid solution in tetrahydrofuran was refluxed with LiAlH4 for 1 hour to obtain menthylmethanol and the solution of menthylmethanol in dimethylformamide was reacted with 1.5 equivalent of SOCl2 at 35℃ under the reduced pressure to afford menthylchloromethane. The total yield of menthylchloromethane was 25.2% based on menthyl chloride.

关 键 词：L-薄荷基氯 L-薄荷基甲酸 L-薄荷基甲基醇 L-薄荷甲基氯 手性合成 

分 类 号：TQ225[化学工程—有机化工]