Hydrochloric Acid → 6-Methyl-2-pyridylmethanol

Participants

Reaction Steps

2-Acetoxymethyl-6-methylpyridine (5 g) was added to saturated hydrochloric acid in methanol (250 ml, prepared by adding 25 ml of acetyl chloride to 225 ml of methanol). The reaction mixture was stirred at room temperature for 18 hours. The solvent was removed under vacuum and the residue was dissolved in dichloromethane (100 ml) and washed with 2N sodium hydroxide solution (3×50 ml). The combined organic layers were washed with brine (1×200 ml), then dried (MgSO4), filtered and evaporated to give the required product as an oil (2.6 g). 1H NMR (250 MHz, CDCl3) δ 2.54 (3H, s), 3.80 (1H, bs), 4.72 (2H, s), 7.04 (2H, d, J=7.7Hz), 7.57 (1H, t, J=7.7Hz).

Provenance & Evidence