Fries rearrangement in methane sulfonic acid, an environmental friendly acid

✍ Scribed by Annie Commarieu; Wolfgang Hoelderich; Jean Alex Laffitte; Marie-Pierre Dupont

• Book ID: 104421818
• Publisher: Elsevier Science
• Year: 2002
• Tongue: English
• Weight: 81 KB
• Volume: 182-183
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/s1381-1169(01)00506-4

✦ Synopsis

The Fries rearrangement of phenyl acetate for the paracetamol process is usually performed in hydrofluoric acid (HF). We have optimized this reaction with methane sulfonic acid (MSA), a strong, stable and biodegradable acid, to give para-hydroxyacetophenone with high conversion and selectivity (up to 92% of para-isomer and 8% of ortho-isomer at 100% conversion).