4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46840872, compound

Participants

Reaction Steps

To a solution of 2-amino-N-(4-sec-butyl-phenyl)-4-methanesulfonyl-benzamide (0.20 g, 0.55 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.13 g, 0.66 mmol) in ethanol (15 mL) was added anhydrous copper (II) chloride (0.222 g, 1.65 mmol). The resulting mixture was stirred at reflux for 24 hours and the solvent was removed using a rotary evaporator. The residue was then diluted with water (50 mL), extracted with ethyl acetate (2×100 mL), and concentrated on using a rotary evaporator. The crude product was made into a slurry in diethyl ether (20 mL) and filtered to provide the title compound as white solid. Yield: 0.20 g (70%). MP 235-237° C. 1H-NMR (400 MHz, CDCl3): δ 8.53 (d, 1H), 8.41 (d, 1H), 8.00 (dd, 1H), 7.16 (d, 2H), 7.06 (d, 2H), 7.00 (s, 2H), 3.91 (m, 2H), 3.80 (m, 2H), 3.15 (s, 3H), 2.59 (m, 1H), 2.13 (s, 6H), 2.04 (m, 1H), 1.58 (m, 2H), 1.22 (d, 3H), 0.73 (t, 3H). MS (ES+) m/z: 521.22 (M+1).

Provenance & Evidence