3,4-Dimethoxybenzophenone → 1-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene

Participants

Reaction Steps

1-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene was prepared analogously to methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate using 3,4-dimethoxybenzophenone (3 g, 12.4 mmol), (ethyl)triphenylphosphonium bromide (5.1 g, 13.6 mmol) and lithium hexamethyldisilazide (13.6 mL, 13.6 mmol, 1M) with a reaction time of 4 hours at room temperature. The crude mixture was purified by flash column chromatography (silica gel, 10% hexane/methylene chloride) to afford 1.3 g (41%) of a mixture of the E and Z isomers as a white solid: mp 72-73° C.; 1H NMR (CDCl3) δ 7.40-6.80 (m, 16 H), 6.16-6.08 (m, 2 H), 3.90-3.80 (m, 12 H), 1.97-1.73 (m, 6 H); 13C NMR (CDCl3) δ 148.6, 148.5, 148.1, 147.8, 142.9, 142.3, 142.0, 140.0, 136.0, 132.5, 129.9, 128.0, 128.0, 127.1, 126.7, 126.6, 123.8, 122.6, 122.5, 119.8, 113.6, 110.8, 110.7, 110.4, 55.8, 55.8, 55.7, 15.7, 15.5; Anal. Calcd for C17H18O2. Theoretical: C, 80.28; H, 7.13. Found: C, 79.94; H, 7.12.

Provenance & Evidence