Hydroxyphenylacetic acid → [(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid

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Reaction Steps

4-Hydroxyphenylacetic acid (760 mg, 4.995 mmol) was dissolved in ethanol (99.5%, 20 ml). Potassium hydroxide (560.5 mg, 9.99 mmol) was added. The mixture was stirred at room temperature for 30 minutes. 2-Bromomethylbenzoic acid methyl ester (1144.2 mg, 4.995 mmol) was then dropped in. The resulting mixture was heated to reflux for 2 hours and then evaporated in vacuum to dry. Water and ethyl acetate were added into the residue and the phases were separated. The water phase was acidified with 10% hydrochloric acid, pH˜5, and then extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and evaporated in vacuum to dry. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/6 ml) using DCM, MeOH/DCM (1:99) as eluant gave the desired product (262 mg), yield 17.5%.

Provenance & Evidence