2-Chloro-4-methylpyridine → 2-Methoxy-4-methylpyridine

Participants

Reaction Steps

Commercially available 2-chloro-4-methylpyridine (25.5 g, 200 mmol) and a sodium methoxide-methanol solution (28.0%, 77.0 g, 399 mmol) were mixed, and the mixture was heated under reflux for 15 hours. After completion of the reaction was confirmed by thin-layer chromatography, the resulting precipitate was filtered out, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was, evaporated under reduced pressure to give 2-methoxy-4-methylpyridine (18.4 g, yield 75%).

Provenance & Evidence