Hydrochloric Acid → 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

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Reaction Conditions

Reaction Steps

The compounds of 5-methoxy-2-methyl-phenol (1.46 g, 9.60 mmol), 3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester (1.00 g, 4.80 mmol), potassium carbonate (1.33 g, 9.60 mmol) are dissolved in dimethylsulfoxide (12 mL) under nitrogen, and the mixture is stirred overnight at 140° C. HCl 10% is added, and the mixture is extracted with diethyl ether. The organic layer is washed with water, dried (Na2SO4) and filtered, and then the solvent is evaporated in vacuo. Purification by flash chromatography by eluting with hexane:ethyl acetate 10:1 to afford the title compound (0.74 g, 47%). Rf=0.44 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.34 (t, 3H, J=7.3 Hz), 2.13 (s, 3H), 2.40 (s, 3H), 3.74 (s, 3H), 4.26 (q, 2H, J=7.1 Hz), 6.28 (d, 1H, J=15.9 Hz), 6.53 (d, 1H, J=2.4 Hz), 6.66-6.73 (m, 3H), 7.15 (d, 1H, J=8.3 Hz), 7.51 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=16.0 Hz).

Provenance & Evidence