Methanol → HCID 14347258, compound

Participants

Reaction Steps

A solution of 3,3-bis[3-(trifluoromethyl)phenyl]-2-propenal (18.5 g) and (carbethoxymethylene)triphenylphosphorane (19.15 g) in methanol (100 mL) was stirred at room temperature for 1 hour. The usual work up furnished a mixture of isomeric esters that was separated by HPLC (hexane-dichloromethane; 2:1) to give 2.8 g of the less polar (Z)-5,5-bis[3-(trifluoromethyl) phenyl]-2,4-pentadienoic acid ethyl ester and 16.8 g of (E)-5,5-bis[3-(trifluoromethyl)phenyl]-2,4-pentadienoic acid ethyl ester. A portion of the (E)-isomer (E)-5,5-bis[3-(trifluoromethyl)phenyl]-2,4-pentadienoic acid ethyl ester was crystallized from hexane to provide the analytical sample, mp 53°-55° C. Anal. Calculated for C21H16F6O2 : C, 60.87; H, 3.89; F, 27.51 Found: C, 61.15; H, 4.04; F, 27.31.

Provenance & Evidence