Citric Acid → 2-[2-(Hydroxymethyl)phenyl]ethanol

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Borane-tetrahydrofuran complex (1M solution in tetrahydrofuran, 100 mL) was added dropwise over 10 minutes, to a solution of 2-carboxymethyl-benzoic acid (6 g) in dry tetrahydrofuran (100 mL) at 0° C., under nitrogen. The resulting mixture was stirred at 0-5° C. for 20 minutes, then warmed to room temperature for 1 hour. Saturated citric acid solution (150 mL) was added and the reaction concentrated to ˜150 mL. The aqueous phase was extracted with ethyl acetate (3×150 mL). The combined organics were washed sequentially with 1M aqueous sodium hydroxide solution (150 mL), water (150 mL), brine (150 mL), dried (sodium sulfate) and evaporated to give the subtitle compound as yellow oil (3.5 g).

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