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

Participants

Reaction Steps

A solution of 4-hydroxybenzoic acid (19.2 g) in 10% NaOH (120 ml) was dropwise added to 480 ml of dimethyl sulfoxide over 30 minutes during which the temeperature in reaction mixture was controlled between 30° and 40° C. After adding, the solution was cooled to 17°-20° C. 1-Bromooctane (28.95 g) was drowise added to the solution over 30 minutes and the reaction mixture was vigorously stirred for 4 hours at room temperature. The reaction mixture was poured into ice water (1200 ml) and acidified with 40 ml of conc. hydochloric acid. After vigorously stirring for 1 hour, the resulting solid was removed by filtration, and dissolved in 60 ml of acetonitrile. The solution was refluxed for 30 minutes, then was allowed to stand overnight at room temperature to yield 4-octyloxybenzoic acid (13.8 g) as crystals (m.p. 96° C.; Anal: Calcd. for C15H22O3 : C 71.97, H 8.86, Found: C 71.30, H 8.89).

Provenance & Evidence