1,3-双(2,4,6-三甲基苯基)氯化咪唑的制备及其催化的安息香缩合反应——推荐一个有机化学设计实验  

Preparation of 1, 3-Dimesityl-1H-Imidazol-3-ium Chloride and Its Application in Benzoin Reaction——Recommendation of An Organic Chemistry Design Experiment for Undergraduate Students

作　　者：吕辉[1] 熊英[1] 龚林波[1] 曹建军[1] 龚淑玲[1] 唐红定[1] LV Hui;XIONG Ying;GONG Lin-bo;CAO Jian-jun;GONG Shu-ling;TANG Hong-ding(National Demonstration Center for Experimental Chemistry Education (Wuhan University),College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China)

机构地区：[1]武汉大学化学与分子科学学院化学国家级实验教学示范中心(武汉大学)

出　　处：《西南师范大学学报（自然科学版）》2019年第9期133-137,共5页Journal of Southwest China Normal University(Natural Science Edition)

基　　金：武汉大学实验技术项目(WHU-2017-SYJS-07)

摘　　要：介绍了一个有机化学设计实验.该实验以乙二醛、 2,4,6-三甲基苯胺、氯甲基乙基醚为原料,通过两步反应高效制得氮杂环卡宾前体盐1,3-双(2,4,6-三甲基苯基)氯化咪唑.然后利用合成的咪唑盐在碱性条件下原位形成的氮杂环卡宾对醛极性反转的特性,催化苯甲醛的安息香缩合反应,合成2-羟基-1,2-二苯基乙酮.使用IR,1H NMR,13 C NMR等多种方法对催化剂及产物结构进行了表征.An organic chemistry design experiment was introduced. The N-heterocyclic carbene precursor(NHC precursor) 1, 3-dimesityl-1 H-imidazol-3-ium chloride was prepared from glyoxal, 2, 4, 6-trimethylaniline and chloromethyl ethyl ether by two steps. The free carbene, which can cause the polarity reversal of an aldehyde, was generated in situ under basic condition to catalyze the benzoin reaction of benzaldehyde to synthesize 2-hydroxy-1, 2-diphenylethanone. The structures of the catalyst and the benzoin product were identified by IR, 1 H NMR, 13C NMR and other methods.

关 键 词：咪唑盐 氮杂环卡宾 极性反转 安息香缩合 有机化学 设计实验 

分 类 号：G642.423[文化科学—高等教育学]