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
匡永清 1刘劼 1冯见君 1杨文 1蔡双莲 1史玲1
作者信息
- 1. 湖南大学化学化工学院,长沙 410082
- 折叠
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.
Abstract
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Key words
Paracetamol/Ketone oximation/Beckmann rearrangement/Organic catalysis引用本文复制引用
出版年
2024
国家科技期刊平台
NSTL
万方数据