Citation: Yongqing Kuang, Jie Liu, Jianjun Feng, Wen Yang, Shuanglian Cai, Ling Shi. Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone[J]. University Chemistry, ;2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012 shu

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

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

Received Date: 3 March 2024
Revised Date: 22 May 2024

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.
- Paracetamol,
- Ketone oximation,
- Beckmann rearrangement,
- Organic catalysis
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