Sodium borohydride → (2-Chloro-6-methylphenyl)methanol

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Reaction Steps

Under ice cooling, 185 mg of sodium borohydride was added to a solution of 1.51 g of 2-chloro-6-methylbenzaldehyde in 15 ml of methanol, followed by stirring for 35 minutes. The reaction mixture was concentrated under reduced pressure and saturated aqueous ammonium chloride was added to the residue. The mixture was extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 1.24 g of 2-chloro-6-methylbenzyl alcohol as colorless crystals.

Provenance & Evidence