3',4'-Dimethoxycinnamic acid → (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dimethoxyphenyl)acrylate

Participants

Reaction Steps

3,4-dimethoxy cinnamic acid (140; 3.82 g; 18.37 mol) was dissolved in 60 mL of dioxane and heated under reflux (60°-70° C.). A catalytic amount (22.5 mg; 0.7 mmol) of tetrabutylammonium bromide and 1.5 g (7.35 mmol) of glycidyl cinnamate (130) were consecutively added to the solution of 3,4-dimethoxy cinnamic acid (140). The resulting mixture was heated to 100°-105° C. with continuous stirring for 15-16 h and then distilled under reduced pressure to yield compound (Id). 1H-NMR (CD3OD) δ 3.81 (s, 3H), 3.83 (s, 3H), 4.14 (m, 1H), 4.27 (d, 4H, J=8 Hz), 6.42 (d, 1H, J=16 Hz), 7.64 (d, 1H, J=16 Hz), 7.15 (dd, 1H, J=8 Hz, 2 Hz), 6.92 (d, 1H, J=8 Hz), 7.18 (d, 1H, J=2 Hz), 6.53 (d, 1H, J=16 Hz), 7.70 (d, 1H, J=16 Hz), 7.35 (m, 3H), 7.56 (m, 2H)

Provenance & Evidence