4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46840873, compound

Participants

Reaction Steps

To a solution of 2-amino-N-(4-sec-butyl-phenyl)-5-methoxy-benzamide (0.450 g, 1.51 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.290 g, 1.51 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.610 g, 4.53 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with dichloromethane (100 mL) and water (100 mL). After separation, the organic phase was further washed with water (100 mL), then brine (100 mL), and dried over sodium sulfate. The crude product was purified by column chromatography on silica gel (230-400 mesh) using hexane/ethyl acetate=1:1 to give the title compound as white solid. Yield: 260 mg (36%). MP 152-154° C. 1H-NMR (400 Hz, CDCl3): δ 7.78 (d, 1H), 7.74 (s. 1H), 7.40 (m, 1H), 7.14 (m, 2H), 7.08 (m, 2H), 6.94 (s, 2H), 3.96 (s, 3H), 3.90 (m, 2H), 3.78 (t, 2H), 2.56 (m, 1H), 2.12 (s, 6H), 2.08 (t, 1H), 1.60 (m, 1H), 1.50 (m, 2H), 1.20 (d, 3H), 0.72 (t, 3H). MS (ES+) m/z: 473.29 (M+1).

Provenance & Evidence