A practical synthesis of 4-chloro-3-(hydroxymethyl)pyridine by regioselective one-pot lithiation/formylation/reduction of 4-chloropyridine

4-Chloro-3-(hydroxymethyl)pyridine was prepared and isolated as its hydrochloride in 85% yield from 4-chloropyridine by formylation with dimethylformamide of the corresponding 3-lithium salt, followed by in situ reduction of the resulting 4-chloro-3-formylpyridine through a crossed-Cannizzaro reaction with aqueous formaldehyde.