4-(Trifluoromethyl)benzaldehyde → 2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester

Participants

Reaction Steps

To a solution of (carbethoxymethylene)triphenylphosphorane (55.3 g, 159 mmol) in 150 mL DCM, alpha,alpha,alpha-trifluoro-p-tolualdehyde (25.00 g, 144 mmol) in 75 mL DCM was added. The reaction is exothermic. The mixture was heated at reflux for 90 minutes. After removing the solvent, hexane was added to the resulting residue. A precipitate appeared and was filtered through filter paper. The collected solid was subjected to a silica gel chromatography with 100% hexane as the eluant to afford a white solid ((E)-ethyl 3-(4-(trifluoromethyl)phenyl)acrylate(25.0 g, yield=71%). LCMS (API-ES) m/z (%): 245.1 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 1.35 (t, J=7.14 Hz, 3H) 4.28 (q, J=7.04 Hz, 2H) 6.68 (d, J=1 6.04 Hz, 1H) 7.70-7.77 (m, 3H) 7.80-7.84 (m, 2H).

Provenance & Evidence