Sulfuric Acid → HCID 136346363, compound

Participants

Reaction Steps

To a flask (ice cooled) containing acetic acid (1.2 ml) was added 5-(2-hydroxy-2-methylpropyl)-2-methoxyphenol (500 mg, 2.5 mmol) and acetonitrile (0.27 ml, 5.1 mmol). To this was added sulfuric acid (1.2 ml) slowly with stirring. The reaction mixture was allowed to warm to rt and stirred for 4 h. The reaction mixture was poured onto ice-water and the aqueous solution neutralised with sodium C(Ar)bonate, then extracted with diethyl ether (2×) and ethyl acetate (2×) after saturation with sodium chloride. Purification (flashmaster: 20 g, 100% DCM to 100% EtOAc, then 30% MeOH/70% EtOAc) afforded the title compound (324 mg, 56%) as a pale brown solid. mp=160° C. dec. 1H NMR (270 MHz; CDCl3) 1.18 (6H, s, 2×CH3), 2.28 (3H, s, CH3), 2.59 (2H, s, CH2), 3.91 (3H, s, OCH3), 6.60 (1H, s, CH), 7.07 (1H, s, CH). 13C NMR (67.5 MHz; CDCl3) 23.21 (CH3), 28.02 (2×CH3), 38.81 (CH2), 53.78 (C(CH3)2), 55.98 (CH3), 110.47 (CH), 112.35 (CH)<121.96 (C), 128.86 (C), 144.35 (C), 148.88 (C), 161.39 (C N). LC/MS (ES+) tr=1.2 min, m/z 219.95 (M++H).

Provenance & Evidence