Diethyl Ether → 2-(3-Methoxyphenyl)-2-propanol

Participants

Reaction Conditions

Reaction Steps

A flame-dried 25 mL R.B. flask equipped with a reflux condenser was charged, under argon, with 3-methoxyacetophenone (1 g, 6.66 mmol) at 0° C. Methylmagnesium iodide in diethylether (4.4 mL, 13.3 mmol, 3M) was then added. The reaction mixture was brought to reflux for 60 min and then cool down to 0° C. and quenched with successive addition of water (5 mL) and saturated ammonium chloride (25 mL). The mixture was extracted with diethyl ether (3×20 mL), the organic extracts were washed successively with 20% sodium bisulfite and saturated sodium bicarbonate, dried, filtered and concentrated. Purification by flash chromatography, using 15% acetone in hexanes, yields propan-2-ol (0.832 g, 75%). 1H NMR (400 MHz, acetone-d6) δ: 1.51 (s, 6H), 3.79 (s, 3H), 6.77 (d, 1H, J=8.1 Hz), 7.07 (d, 1H, J=7.7 Hz), 7.13 (s, 1H), 7.22 (t, 1H, J=7.9 Hz).

Provenance & Evidence