4-Aminophenol → Acetaminophen

Participants

Reaction Steps

This example shows the stepwise reduction of p-nitrophenol and acetylation of p-aminophenol to produce the N-acetyl-p-aminophenol according to this invention: 90 grams of p-nitrophenol was added to 243 ml of water containing 1.25 grams charcoal and 0.31 grams catalyst (50% catalyst 50% water) of 5% palladium-on-charcoal. The system was heated to 95°-98° C. and hydrogen pressure of 70 psig. After 1 hour hydrogenation, the batch was cooled to 48° C. (pH 5.8) and 35 grams acetic anhydride was added. The reduction was continued at 95°-98° C. and 70 psig until hydrogen uptake ceased. The batch was cooled to 40° C. (pH 5.0) and 35 grams of acetic anhydride was added with heating to 95° C. The batch was filtered to recover catalyst. The N-acetyl-p-aminophenol was crystallized to yield a white crystalline product. Quality of the APAP was good giving only a slight pink caustic test and the product yield was 81.2 %.

Provenance & Evidence