Hydrochloric Acid → 1-(4-Methyl-3-nitrophenyl)ethan-1-ol

Participants

Reaction Steps

To a solution of 1-(4-methyl-3-nitrophenyl)ethan-1-one (2.00 g) in ethanol/tetrahydrofuran (15 mL/7.5 mL) was added sodium borohydride (211 mg), and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture were added 0.5 mol/L hydrochloric acid and water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain the title compound (1.96 g). 1H-NMR (CDCl3) δ ppm: 1.52 (3H, d, J=6.5 Hz), 1.84-1.95 (1H, m), 2.59 (3H, s), 4.91-5.02 (1H, m), 7.32 (1H, d, J=7.9 Hz), 7.52 (1H, dd, J=1.8, 7.9 Hz), 7.99 (1H, d, J=1.8 Hz).

Provenance & Evidence