Methyl 3-methoxy-5-nitrobenzoate → (3-Methoxy-5-nitrophenyl)methanol

Participants

Reaction Steps

Lithium aluminum hydride (0.1116 g, 2.94 mmol, 1.5 eq) was added to a stirred solution of methyl 3-methoxy-5-nitrobenzoate (0.408 g, 1.96 mmol, 1 eq) in 10 ml anhydrous Et2O at 0° C. under Ar. The reaction was stirred at 0° C. to room temperature overnight. Starting material was still present after stirring overnight. Additional LAH (0.1116 g, 2.94 mmol, 1.5 eq) was added. After 2 h the reaction was quenched with water. The reaction was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with brine (×1) and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.2463 g (1.33 mmol, 68% yield) of (3-methoxy-5-nitrophenyl)methanol.

Provenance & Evidence