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, was added α,α,α-trifluoro-p-tolualdehyde (25.00 g, 144 mmol)(commercially available from 3B Scientific Corporation Product List (Order Number 3B4-3644)) in 75 mL DCM. The reaction was 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 collected by filtration through filter paper. The collected solid was subjected to silica gel chromatography with 100% hexane as the elutant 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=16.04 Hz, 1H) 7.70-7.77 (m, 3H) 7.80-7.84 (m, 2H).

Provenance & Evidence