Acetic Anhydride → [3-(Acetyloxy)phenyl]acetic acid

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 3-hydroxyphenylacetic acid (10.2 g; 67 mmol) in acetic anhydride (100 mL; 1.06 mol) under anhydrous conditions was treated with pyridine (0.5 mL). In the mildly exothermic reaction, the solids dissolved within several minutes and the mixture was maintained at 40° C. for five hours. The reaction was concentrated in vacuo to about half volume, then water (30 g) in the form of ice chips was added at such a rate that the temperature remained <45° C. When the exotherm had subsided, a second portion of water (200 mL) was added slowly and the mixture was stirred for another 30 minutes. The precipitated solid was filtered, washed with water and dried to constant weight in vacuo over P2O5 to give 3-acetoxyphenylacetic acid (11.7 g) which was used without further purification.

Provenance & Evidence