3-Methyl-2-nitrophenylacetic acid → 2-(3-Methyl-2-nitrophenyl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 1.2 g (6 mmol) 3-methyl-2-nitro-phenylacetic acid and 24 mL anhydrous THF. The reaction was cooled to 0° C. and then treated with 4.0 mL 2M BH3-DMS in THF (7.8 mmol) over 5 m. The reaction was allowed to warm to rt overnight. The volatile solvents were removed in vacuo and the resulting material was partitioned between EtOAc/1 M NaHCO3. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 1.06 g (95% yield) as a light, orange oil. 1H NMR (400 MHz, CDCl3) δ 7.32–7.16 (m, 3H), 3.84 (t, J=6.4 Hz, 2H), 2.81 (t, J=6.4 Hz, 2H), 2.30 (s, 3H).

Provenance & Evidence