Hydrochloric Acid → HCID 54281005, compound

Participants

Reaction Steps

A solution of 2'-methoxy-5'-tert-butylstilbene-4-methanol (5.83 g, 19.7 mmol) in 1,4-dioxane (25 ml) was poured into concd. hydrochloric acid (120 ml). A colourless precipitate appeared immediately. The mixture was stirred for 1 h. Then dichloromethane (250 ml) was added. The organic layer was washed with water (500 ml), brine (250 ml), dried over anhydrous magnesium sulfate, filtered and concentrated vacuo. The residue was purified by column chromatography over silica (dichloromethane) and by recrystallisation from hot hexane to yield (19) (4.26 g, 69%) in form of colourless crystals, m.p. 103°-104° C.; (Found: C, 76.42; H, 7.42. C20H24ClO requires C, 76.30; H, 7.36%); δH (CDCl3) 1.40 (9 H, s, tert-butyl), 3.90 (3 H, s, OCH3), 4.62 (2 H, s, CH2Cl), 6.88 (1 H, d, J=8.7 Hz, Phil), 7.17 (1 H, d, J=16.5 Hz, vinylic H), 7.32 (1 H, dd, J=8.6, 2.5 Hz, PhH), 7.40 and 7.57 (4 H, AA'BB', PhH), 7.54 (1 H, d, J=16.0 Hz, vinylic H), 7.65 (1 H, d, J=2.4 Hz, PhH); m/z 316, 314 (35, M+), 301, 299 (29, 91%).

Provenance & Evidence