由4-羟基苯乙酮制备对乙酰氨基酚的两步合成实验设计
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。...
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| Published in | 大学化学 Vol. 39; no. 8; pp. 331 - 337 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | Chinese |
| Published |
北京大学
28.08.2024
中国化学会 湖南大学化学化工学院,长沙 410082 |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1000-8438 |
| DOI | 10.12461/PKU.DXHX202403012 |
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| Abstract | 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。 |
|---|---|
| AbstractList | 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。 G64%O6; 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_FL | 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. |
| Author | 蔡双莲 冯见君 史玲 杨文 匡永清 刘劼 |
| AuthorAffiliation | 湖南大学化学化工学院,长沙 410082 |
| AuthorAffiliation_xml | – name: 湖南大学化学化工学院,长沙 410082 |
| Author_FL | Jianjun Feng Wen Yang Shuanglian Cai Ling Shi Yongqing Kuang Jie Liu |
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| DocumentTitle_FL | Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone |
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| Keywords | 有机催化 酮肟化 对乙酰氨基酚 Beckmann重排 Paracetamol Organic catalysis Beckmann rearrangement Ketone oximation |
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