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

Participants

Reaction Steps

A solution of p-hydroxybenzoic acid (19.2 g, 150 mmoles) in 10% aqueous sodium hydroxide (120 ml) is added to dimethyl sulfoxide (DMSO) (480 ml) previously heated to 80° C. n-Octyl bromide (28.95 g, 150 mmoles) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml). Conc. hydrochloric acid (30 ml) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. mp 97°-99° C.

Provenance & Evidence