Acetic Anhydride → 2-Acetoxymethyl-6-chloropyridine

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Reaction Steps

A solution of the 6-chloro-2-methylpyridine-N-oxide prepared in step 1 in 750 mL acetic anhydride was heated at reflux overnight. The reaction was cooled to ambient temperature and poured into saturated aqueous sodium bicarbonate. The mixture was diluted with ethyl acetate and filtered through celite. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated. The residue was azeotroped with benzene to remove any remaining acetic acid. 2-acetoxymethyl-6-chloropyridine was isolated by vacuum distillation (b.p. 105°-110° C./1.3 torr).

Provenance & Evidence