Hydrochloric Acid → 4-(Benzyloxy)benzoic acid

Participants

Reaction Steps

To a suspension of 15.0 g of methyl 4-benzyloxybenzoate in 225 ml of methanol were added 18.6 ml of a 5N solution of sodium hydroxide. The mixture was heated at reflux for 18 hours. The solution was cooled to room temperature and acidified to pH 3 by addition of 6N hydrochloric acid. The resulting white precipitate was filtered to give 13.6 g of the title compound: 300-MHz 1H NMR (DMSO-d6) δ5.18 (s, 2H), 7.04 (d, J=9 Hz, 2H), 7.26-7.49 (m, 5H), 7.86 (d, J=9 Hz, 2H), 12.3 (b s, 1H).

Provenance & Evidence