Methanol → 5-(Hydroxymethyl)-2-nitrophenol

참여 물질

반응 단계

To a solution of 3-hydroxy-4-nitrobenzoic acid (50.0 g, 0.273 mol) in dichloroethane (1000 mL) under a nitrogen atmosphere were added trimethoxyborane (45.4 g, 0.437 mol) and boron trifluoride diethyl etherate (62.0 g, 0.437 mol) followed by dropwise addition of borane-pyridine complex (38.1 g, 0.410 mol). After stirring at room temperature for 4 hours, methanol (100 mL) was added dropwise under cooling in an ice-bath. The mixture was concentrated under reduced pressure and toluene (400 mL) was added to the residue. The resulting mixture was extracted with aqueous 1N NaOH solution (300 mL×3), and the combined aqueous lavers were acidified with conc. hydrochloric acid to pH 1 and extracted with ethyl acetate (500 mL and 300 mL). The organic layers were combined, washed with water (300 mL×2) and brine successively aid dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give B-3 (43.3 g, 94%).

출처 및 근거