Fries rearrangement in methane sulfonic acid, an environmental friendly acid

Author(s): Commarieu A, Hoelderich W, Laffitte JA, Dupont MP

Abstract

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).

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