4-Hydroxyphthalic acid → 4-(4-Fluoro-benzyloxy)-phthalic acid

Participants

Reaction Steps

A mixture of 4-hydroxyphthalic acid (5.0 g, 27 mmol), potassium hydroxide (5.4 g, 30 mmol) and 4-fluorobenzylbromide (5.7 g, 30 mmol) in water (13 mL) was heated under reflux for 5 h. After cooling to room temperature, the mixture was washed with ether. The aqueous phase was then acidified to pH 2 at 0° C. with concentrated HCl and then extracted with ethyl acetate. The organic extracts were then washed with water and dried over sodium sulfate. Filtration and evaporation gave a residue which was purified by chromatography (SiO2, CHCl3:Acetone:AcOH: 90:9:1) to afford the title compound (2.3 g, 29%) as a colorless oil. MS: m/e=289.0 (M−H+).

Provenance & Evidence