Water → (2-Methoxy-6-methylphenyl)methanol

Participants

Reaction Steps

To a solution of ethyl 2-methoxy-6-methylbenzoate (1.23 g, 6.33 mmol) in dry diethyl ether (58 mL) was added LiAlH4 (0.467 g, 12.31 mmol) and the resultant mixture was heated to reflux for 2 hours then cooled to room temperature. The mixture was treated sequentially with water (0.45 mL), 15% aqueous NaOH (0.45 mL) and water (1.35 mL). The mixture was filtered through Celite© and the cake was washed with ether (200 mL). The filtrate was concentrated under reduced pressure and provided 0.96 g (99%) of 2-methoxy-6-methylbenzyl alcohol as a yellow solid. 1H NMR (CDCl3) δ 2.27 (t, 1H, J=6.3 Hz), 2.39 (s, 3H), 3.86 (s, 3H), 4.75 (d, 2H, J=6.3 Hz), 6.76 (d, 1H, J=8.4 Hz), 6.81 (d, 1H, J=7.8 Hz), 7.17 (dd, 1H, J=7.8, 8.4 Hz).

Provenance & Evidence