Ethanol → Methyl 4-(hydroxymethyl)-2-methylbenzoate

Participants

Reaction Steps

A mixture of methyl 4-formyl-2-methylbenzoate (200 mg, 1.1 mmol), sodium borohydride (210 mg, 5.5 mmol) and ethanol (10 mL) was stirred at room temperature for 4 hours. To the resultant mixture, water (0.4 mL) was added. The organic phase was separated, concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give methyl 4-(hydroxymethyl)-2-methylbenzoate (126 mg, 64%). 1H NMR (300 MHz, d6-DMSO): δ 7.78 (d, J=7.8 Hz, 1H), 7.15 (dd, J=7.8 Hz, J=1.8 Hz, 1H), 7.06 (d, J=1.8 Hz, 1H), 5.39 (t, J=5.7 Hz, 1H), 4.79 (d, J=5.7 Hz, 2H), 3.88 (s, 3H), 2.35 (s, 3H).

Provenance & Evidence