Sodium sulfate decahydrate → 5-Chloro-2-(hydroxymethyl)phenol

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Reaction Steps

1.65 g of lithium aluminum hydride were suspended in 100 ml of tetrahydrofuran, and then 5.00 g of 4-chlorosalicylic acid in 50 ml of tetrahydrofuran were added dropwise to the resulting suspension, whilst stirring and ice-cooling. The resulting mixture was then heated under reflux for 1 hour. At the end of this time, the reaction mixture was cooled on ice, and sodium sulfate decahydrate was added to decompose the excess hydride. Insoluble substances were removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The residue was then purified by silica gel column chromatography, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.00 g (yield 87%) of the title compound as a colorless solid substance.

Provenance & Evidence