Hydrochloric Acid → Cinnamic acid, p-hydroxy-, acetate

Participants

Reaction Steps

To a mixture of 16.5 g (0.101 mol) of 4-hydroxycinnamic acid and 200 ml of a THF solution of 24 ml (0.297 mol) of pyridine was dropwise added 20 ml (0.281 mol) of acetyl chloride over 1 hour at room temperature. After the resulting mixture was stirred at room temperature for 7 hours, the reaction system was poured into 300 ml of a 2N aqueous solution of hydrochloric acid. After extracting with ether and concentrating the organic phase, there was obtained 13.14 g (0.064 mol) of 4-acetoxycinnamic acid as a white solid. The yield was 63%.

Provenance & Evidence