Oxygen → 4-Fluoro-2-(hydroxymethyl)phenol

Participants

Reaction Conditions

Reaction Steps

With exclusion of oxygen, 27.1 g (159.28 mmol) of methyl 5-fluoro-2-hydroxybenzoate are introduced into 500 ml of dry THF and cooled to 0° C. Then, while cooling, 238 ml (238 mmol) of a 1 M solution of lithium aluminum hydride in THF are slowly added dropwise, and the mixture is stirred at 0° C. for 1 hour and then at RT overnight. After reaction is complete, the mixture is mixed with saturated ammonium chloride solution and taken up in methylene chloride, and the organic phase is separated off and dried over sodium sulfate. After filtration, the solvent is removed in vacuo. The crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1). 18.0 g (126.6 mmol, 79% yield) of a colorless solid are isolated.

Provenance & Evidence