Benzyl Alcohol → 2-(Benzyloxy)pyridine-4-carboxylic acid

Participants

Reaction Steps

To a suspension of sodium hydride (14.0 g) in N,N-dimethylformamide (250 mL) was added dropwise benzyl alcohol (20.6 g) under ice-cooling over 30 minutes and then added 2-chloroisonicotinic acid (25.0 g) thereto. The reaction solution was stirred at room temperature for 2 hours and then at 70° C. for 13 hours. The reaction solution was allowed to cool to room temperature, diluted with about decuple volumes of water, and then adjusted to pH 5 with 5N hydrochloric acid. The resulting crystals were collected by filtration and then washed with water and hexane to give the title compound as a colorless solid (12.6 g).

Provenance & Evidence