3,5-Dimethyl-4-hydroxybenzaldehyde → HCID 59248994, compound

Participants

Reaction Steps

A solution of 1-(5-methyl-4-phenyl-thiophen-2-yl)-ethanone (419 mg, 1.94 mmol) and 3,5-dimethyl-4-hydroxybenzaldehyde (350 mg, 2.33 mmol) in ethanol (4 mL) and 5 N HCl in isopropanol (2 mL) is stirred at it for 1 h. The dark green solution is diluted with water and extracted with EA. The organic extract is evaporated, dissolved in ethanol (10 mL) and treated with Pd/C (60 mg, 10% Pd). The slurry is hydrogenated under 1.4 bar of H2 for 6 h. The mixture is filtered, the solvent is removed in vacuo and the crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-methyl-4-phenyl-thiopen-2-yl)-propan-1-one (360 mg) as a colourless resin; LC-MS: tR=1.09 min, [M+1]+=351.25; 1H NMR (CDCl3): δ 7.60 (s, 1H), 7.46-7.30 (m, 5H), 6.85 8s, 2H), 4.48 (s, 1H), 3.14 (dd, J=7.0, 8.2 Hz, 2H), 2.92 (dd, J=7.0, 8.2 Hz, 2H), 2.52 (s, 3H), 2.21 (s, 6H).

Provenance & Evidence