4-Hydroxybenzoic Acid → Methylparaben

Participants

Reaction Steps

To a solution of 4-hydroxybenzoic acid (138 g, 1.00 mol) in methanol (1000 mL) was added concentrated sulfuric acid (20 mL), then the reaction heated at reflux for 20 h. The reaction mixture was concentrated to one half the original volume under reduced pressure then partitioned with ethyl acetate (1000 mL) and water (1000 mL). The organic layer was washed with 1 N aqueous sodium hydroxide (2×300 mL), water (300 mL), brine (300 mL) then dried (MgSO4). The solvent was removed under reduced pressure to give the ester as a white solid (106.62 g, 70%) after drying under vacuum at ambient temperature.

Provenance & Evidence