由4-羟基苯乙酮制备对乙酰氨基酚的两步合成实验设计  

Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone

作　　者：匡永清[1] 刘劼 冯见君 杨文 蔡双莲[1] 史玲[1] Yongqing Kuang;Jie Liu;Jianjun Feng;Wen Yang;Shuanglian Cai;Ling Shi(College of Chemistry and Chemical Engineering,Hunan University,Changsha 410082,China)

机构地区：[1]湖南大学化学化工学院,长沙410082

出　　处：《大学化学》2024年第8期331-337,共7页University Chemistry

基　　金：湖南省普通高校教学改革研究立项项目(HNJG-2020-0109)。

摘　　要：设计了由4-羟基苯乙酮制备对乙酰氨基酚的两步合成实验,并应用于本科教学。先由4-羟基苯乙酮与羟胺缩合产生4-羟基苯乙酮肟,再由三聚氯氰催化4-羟基苯乙酮的Beckmann重排反应得到对乙酰氨基酚。实验应用了回流、萃取、干燥、过滤、旋转蒸发、薄层色谱和柱层析等重要有机实验操作,可综合训练学生的有机合成技术。通过制备具有重要医学和经济价值的目标化合物,向学生展示了有机合成技术在实际生活中的应用,有利于提高他们学习有机化学的兴趣。Beckmann重排采用了有机小分子催化剂,有助于学生加深理解有机催化的意义和Beckmann重排反应的机理。A two-step synthetic experiment to produce paracetamol from 4-hydroxyacetophenone was designed for undergraduate organic chemistry courses.The experiment begins with the condensation of 4-hydroxyacetophenone with hydroxylamine to form 4-hydroxyacetophenone oxime.This oxime then undergoes a Beckmann rearrangement catalyzed by cyanuric chloride to yield paracetamol.The experiment incorporates several essential organic laboratory techniques,such as reflux,extraction,drying,filtration,rotary evaporation,thin-layer chromatography,and column chromatography,providing students with comprehensive training in organic synthesis.By synthesizing a compound of significant medical and economic value,the experiment demonstrates practical applications of organic synthesis,thereby enhancing student interest in organic chemistry.Additionally,the use of a small molecule organic catalyst for the Beckmann rearrangement deepens students’understanding of the principles of organic catalysis and the mechanism of the Beckmann rearrangement.

关 键 词：对乙酰氨基酚 酮肟化 BECKMANN重排 有机催化 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]