Acetic Anhydride → 2-[2-Hydroxy-3-(o-tolyloxy)phenyl]glycine

Participants

Reaction Steps

2-[2-Methoxy-3-(o-tolyloxy)phenyl]glycine (22.4 g) was added to a mixture of acetic anhydride (75 ml) and hydriodic acid (55-58%, 150 ml), and the mixture was refluxed under heating for 9 hours. The reaction mixture was poured into water (1 l) and adjusted to pH 12 with 20% aqueous sodium hydroxide. The solution was washed with diethyl ether and adjusted to pH 6.0 with conc. hydrochloric acid. The precipitating crystals were collected by filtration washed with water and dried to give 2-[2-hydroxy-3-(o-tolyloxy)phenyl]glycine (1500 g). mp 170°-173° C.

Provenance & Evidence