6-Methyl-2-nitrobenzoic acid → (2-Methyl-6-nitrophenyl)methanol

Participants

Reaction Steps

A 100 mL round bottomed flask under dry argon was charged with 5 g of 2-methyl-6-nitrobenzoic acid which was dissolved in 60 mL of dry tetrahydrofuran. To this solution was added slowly with cooling and stirring, 64.17 mL of a 1M solution of BH3.THF in THF. The mixture was refluxed for 17 h then the reaction was slowly and carefully quenched with an excess of 10% aqueous hydrochloric acid. The THF was removed under vacuum and the residue was extracted with three 50 mL aliquots of methylene chloride. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and the solvent removed. The crude product was recrystallized from methylene chloride/pentane to give 4.95 g of yellowish crystals (97% yield).

Provenance & Evidence