4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46840740, compound

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Reaction Steps

Anhydrous CuCl2 (0.21 g, 1.6 mmol) was added to a solution of 2-amino-N-(4-sec-butylphenyl)-5-fluorobenzamide (0.15 g, 0.52 mmol), and 4-(2-hydroxyethoxy)-3,5-dimethyl-benzaldehyde (0.12 g, 0.63 mmol) in ethanol (30 mL). The resulting green solution was heated at reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under vacuum. The residue was stirred with water (20 mL), and extracted with ethyl acetate (2×25 mL). The organic layer was separated, washed with brine, and dried over Na2SO4. The solvent was evaporated under vacuum, and the residue was purified by flash column chromatography on a Biotage (25 M silica column) using a gradient of hexane:ethyl acetate (8:2 to 5:5) mixture as eluent to afford the title compound. Yield: 0.19 g (77%). MP 70-72° C. 1H-NMR (400 MHz, CDCl3): 7.99 (m, 1H), 7.82 (m, 1H), 7.53 (m, 1H), 7.15 (m, 2H), 7.09 (d, 2H), 6.97 (s, 2H), 3.91 (m, 2H), 3.78 (m, 2H), 2.59 (m, 1H), 2.15 (s, 6H), 2.02 (t, 1H), 1.54 (m, 2H), 1.21 (d, 2H), 0.73 (t, 3H).

Provenance & Evidence