Hydrochloric Acid → alpha-Methyl-3-nitrobenzenemethanol

Participants

Reaction Conditions

Reaction Steps

40 g of 3-nitrophenylacetic acid was added to a solution of 26 ml of 10M borane-methyl sulfide in 200 ml of THF, and the mixture was stirred at 25° C. for 3 hr. The solution was then acidified with HCl in methanol, followed by evaporation of the solvent. The product 3-nitrophenylethanol (IV, A=H) was partitioned between diethyl ether (Et2O) and aqueous sodium carbonate, and the Et2O layer dried over sodium sulfate. Evaporation of the Et2O afforded 34.8 g of 3-nitrophenylethanol (IV, A=H) as an oil.

Provenance & Evidence