Borane → (2-Methyl-4-nitrophenyl)methanol

Participants

Reaction Steps

To a solution of 5.08 g (27.2 mmol) 2-methyl-4-nitrobenzoic acid in 50 ml dry THF, 41 ml (41 mmol) borane-THF complex (1M solution in THF) is added drop-wise at 0° C. After completion of the borane addition, the reaction mixture is stirred at room temperature for 20 h. After that a K2CO3 solution (1.33 g in 49 ml water) is slowly added under stirring. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is taken up in diethylether, vigorously stirred, and the title compound is obtained after filtration as a yellow crystalline solid.

Provenance & Evidence