4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46841007, compound

Participants

Reaction Steps

To a solution of 2-amino-N-(4-bromo-phenyl)-5-methoxy-benzamide (0.240 g, 0.740 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.145 g, 0.740 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.298 g, 2.22 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with ethyl acetate (100 mL) and water (100 mL). After separation the organic phase was further backwashed with water (100 mL), brine (100 mL), dried over sodium sulfate, and concentrated. The crude was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1) to give the title compound as white solid. Yield: 120 mg (33%). MP 160-162° C. 1H-NMR (400 Hz, CDCl3): δ 7.74 (d, 1H), 7.69 (s, 1H), 7.46 (d, 2H), 7.40 (m, 1H), 7.03 (d, 2H), 6.96 (s, 2H), 3.94 (s, 3H), 3.91 (m, 2H), 3.82 (t, 2H), 2.17 (s, 6H), 2.05 (t, 1H). MS (ES+) m/z: 497.41 (M+1).

Provenance & Evidence