Sodium Hydroxide → 4-(Benzyloxy)benzoic acid

Participants

Reaction Steps

A solution of methyl 4-benzyloxybenzoate (4.2 g, 17.3 mmole) and sodium hydroxide (15 mL of 2N) in methanol (200 mL) was heated at reflux for 24 hours. The methanol was removed under vacuum and water (200 mL) was added to the resulting residue. The mixture was acidified to pH 3 by the dropwise addition of concentrated hydrochloric acid. The resulting precipitate was isolated by filtration, washed with cold water and dried to provide 3.1 g of 4-benzyloxybenzoic acid as a white powder, m.p. 186°-187° C.

Provenance & Evidence