4-Nitro-o-toluic acid → (2-Methyl-4-nitrophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-4-nitrobenzoic acid (5 g, 27.6 mmol, Aldrich) in THF) (95 ml) was added dropwise 1.0 M borane-tetrahydrofuran complex (55 ml, 55.0 mmol, Aldrich) at ambient temperature under nitrogen. The resulting red solution was heated to 80° C. for 2 h. To the solution at ambient temperature was added methanol (30 ml) and then heated to 80° C. for 30 min. The solvent was evaporated in vacuo to leave a yellow oil. The residue was dissolved in methanol (80 ml) and the solvent evaporated in vacuo to leave (2-methyl-4-nitrophenyl)methanol as a yellow solid (4.73 g).

Provenance & Evidence