4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46841008, compound

Participants

Reaction Steps

To a solution of 2-amino-N-(4-bromo-phenyl)-3-methoxy-benzamide (0.600 g, 1.86 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.360 g, 1.86 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.750 g, 5.58 mmol). The reaction mixture was stirred at reflux for 16 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), then brine (100 mL), dried over sodium sulfate, and concentrated. The crude product was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1) to give the title compound as a white solid. Yield: 250 mg (27%). MP 100-102° C. 1H-NMR (400 Hz, CDCl3): δ 7.90 (d, 1H), 7.47 (m, 3H), 7.25 (m, 1H), 7.03 (d, 2H), 7.00 (s, 2H), 4.02 (s, 3H), 3.91 (m, 2H), 3.80 (t, 2H), 2.15 (s, 6H), 2.06 (t, 1H). MS (ES+) m/z: 497.41 (M+1).

Provenance & Evidence