Methanol → 2-(4-Nitrophenyl)butanol

Participants

Reaction Steps

To a solution of 20.9 g of 2-(4-nitrophenyl)butyric acid in 500 ml of dry tetrahydrofuran was added, dropwise, 1.1 equivalents of 10 M borane-dimethylsulfide complex in 100 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 1.5 hours and then refluxed for 1.5 hours and finally cooled to room temperature. Methanol (10 ml) was added, the mixture was stirred for 30 minutes, and the solvent was then evaporated under reduced pressure. The residue was dissolved in 100 ml of methanol and the solvent was evaporated and this procedure was repeated three (3) times. The resulting oil was purified by chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane to give 2-(4-nitrophenyl)butanol as a light-yellow oil.

Provenance & Evidence