4-Hydroxybenzoic Acid → 4-(Benzyloxy)benzoic acid

Participants

Reaction Steps

KOH (6.16 g, 109.78 mmol) and benzyl bromide (9.42 g, 55.08 mmol) were added to a stirred solution of 4-hydroxy benzoic acid (6.9 g, 49.96 mmol) in EtOH:H2O (9:1, 176 mL) and the resulting mixture was heated to reflux for 20 hrs. 20% KOH solution (60 mL) was then added the mixture maintained at reflux for 4 hours. The reaction mixture was diluted with water (200 mL) and acidified with 20% HCl. The resulting white precipitate was filtered and washed with water followed by hexane to afford 7.1 g (62.2% yield) of 4-benzyloxy benzoic acid. 1H NMR (DMSO-d6): δ 12.6 (s, 1H), 7.9 (d, 2H), 7.4 (m, 5H), 7.1 (d, 2H), 5.2 (s, 2H).

Provenance & Evidence