Water → p-Methylphenoxyacetic acid

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.86 g of 60% NaH in oil=0.516 g, 21.5 mmol) in oil dispersion was washed twice with 10 ml of hexane. THF was added (5 ml) and the mixture was cooled to -15° C. A solution of p-methylphenol (1.95 g, 18 mmol) in THF was then added, and the mixture was warmed to 25° C. for 1 hour. The THF was removed by distillation under vacuum and a solution of sodium chloroacetate (2.5 g, 22 mmol) in DMSO (50 ml) was added. The mixture was stirred at room temperature for 20 hours, then diluted with 300 ml. of water. The mixture was extracted twice with 50 ml. of hexane. The aqueous phase was acidified with 4N hydrochloric acid and the product was extracted twice with 100 ml. of ethyl acetate. The combined ethyl acetate layers were washed twice with 100 ml. water, dried over MgSO4, filtered, and the solvent was removed by distillation under reduced pressure to give 2.9 g of product as a white solid. Yield of product=97.6%.

Provenance & Evidence