摘要
介绍一个探索型多步有机合成实验。以邻苯二甲酸二乙酯为原料,经过Claisen缩合、水解、脱羧、亚硝化、脱肟、还原、氧化等反应,再经重结晶,制备目标产物水合茚三酮。最后通过熔点测定、红外光谱、核磁共振对产物结构进行表征。实验包括回流、控温、过滤、重结晶、干燥、熔点测定、红外光谱和核磁共振图谱测试等基本操作。此实验设计不仅巩固了本科生在有机合成实验中的基本操作,而且培养了学生在应对多步有机合成反应中的综合实验能力。
Synthesis of ninhydrin through a multistep reaction was developed as an organic chemistry laboratory experiment for upper-division undergraduate students.The bright yellow ninhydrin solid was synthesized using diethyl phthalate as the feedstock via a sequence organic process including Claisen condensation,hydrolysis,decarboxylation,nitrosation,deoxime,reduction,and oxidation.In this experiment,various hands-on experimental organic synthetic techniques,such as reflux,temperature control,filtration,vacuum drying,recrystallization were utilized.Moreover,melting point test,IR and NMR spectra were used to characterize the final product.The design of ninhydrin synthesis experiment is helpful to improve the fundamental operation capability and experimental skills of the upper-division undergraduate students.
作者
姜爽
靳晓宁
张万东
Jiang Shuang;Jin Xiaoning;Zhang Wandong(School of Science,Tianjin University,Tianjin 300354,China;National Demonstration Center for Experimental Chemistry&Chemical Engineering Education,Tianjin University,Tianjin 300354,China;National Virtual Simulation Experimental Teaching Center for Chemistry&Chemical Engineering Education,Tianjin University,Tianjin 300354,China)
基金
2020年天津市普通高等学校本科教学质量与教学改革研究计划项目(项目编号:B201005607)。
关键词
邻苯二甲酸二乙酯
水合茚三酮
多步合成
diethyl benzene-1,2-dicarboxylate
2,2-dihydroxyindane-1,3-dione(ninhydrin)
multistep synthesis
