Nitric Acid → [3-nitro-4-(trifluoromethyl)phenyl]methanol

Participants

Reaction Steps

4-(Trifluoromethyl)benzoic acid (15 g, 78.9 mmol) in 90 mL of concentrated sulfuric acid was treated dropwise with a mixture of fuming nitric acid (2 mL) and sulfuric acid (24 mL). The reaction mixture was stirred at ambient temperature for 48 hours and quenched into ice-water. The resulting precipitate (12 g) was collected by filtration, washed with water and dried under reduced pressure. The resulting dry solid (12 g) was dissolved in THF (300 mL), cooled to 0° C., treated with 1M borane-tetrahydrofuran complex (80 mL) and stirred at ambient temperature overnight. Methanol (5 mL) was added dropwise followed by dropwise addition of concentrated HCl (5 mL), refluxed for 1 hour and evaporated to dryness and partitioned between water and diethyl ether. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 30% ethyl acetate hexanes to provide the title compound (3.6 g, 20% yield).

Provenance & Evidence