关键词: 对乙酰氨基酚, 酮肟化, Beckmann重排, 有机催化

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.

Key words: Paracetamol, Ketone oximation, Beckmann rearrangement, Organic catalysis