Hydrochloric Acid → 5-Chloro-2-(hydroxymethyl)phenol

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Reaction Steps

To 7 g of LiAlH4 in 200 ml of THF is added portionwise 15 g of 4-chlorosalicylic acid. The resulting mixture is heated under reflux for one hour, cooled and stirred at room temperature for 21 hours. Water (7 ml) in THF (50 ml) is added dropwise, followed by 1N hydrochloric acid (250 ml), concentrated hydrochloric acid (50 ml) and ethyl acetate (200 ml). After filtration on a pad of celite the two layers are separated, the organic layer washed with brine, dried over magnesium sulfate, concentrated. The brown oil is dissolved in iso-propyl ether and filtered on a short column of silica gel. After concentration the solid is crystallized in cyclohexane, filtered, washed and dried to give 4-chloro-2-hydroxy-benzylalcohol as a white solid (9.7 g, 70% yield) C7H7ClO2 MS (M+) m/z: 158, 160, Cl pattern.

Provenance & Evidence