Phenol → Phenyl acetate

Participants

Reaction Steps

Phenol was acetylated with a 1.5 times molar excess of acetyl chloride at room temperature, the excess acetyl chloride being removed by evaporation under reduced pressure. A very high yield of phenyl acetate was produced. To this reaction product a 2.4 times molar excess of acetic anhydride was added with stirring, followed by a 1.5 times molar excess of sulphuric acid added dropwise at 50° C. over 30 minutes. After stirring for a further 60 minutes, the mixture was neutralised using a 1.5 time molar excess of sodium acetate in glacial acetic acid solution. Trituration of the reaction mixture with ether followed by filtration resulted in a dry yellow solid. This was recrystallised from methanol and washed with sodium carbonate solution. A 99% conversion to sodium sulphonatophenyl acetate was achieved.

Provenance & Evidence