Acetic Anhydride → (4-Chloro-3-methylpyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

50 ml of acetic anhydride was added to 5.63 g of 4-chloro-2,3-dimethylpyridine-N-oxide (VI) and the resulting mixture was heated at 110° C. for 1 hour. The solvent was distilled off under reduced pressure and water was added thereto and the resulting mixture was extracted with ether. The resulting organic layer was washed with water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 90% ethanol, and 2.10 g of sodium hydroxide was added thereto, and the resulting mixture was heated at 80° C. for 3 hours. The solvent was distilled off under reduced pressure, and thereafter, water was added thereto and the resulting mixture was extracted with chloroform. The resulting organic layer was washed with saturated salt water, and then dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; chloroform) to obtain 1.69 g of 4-chloro-2-hydroxymethyl-3-methylpyridine (VII).

Provenance & Evidence