4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)but-2-enoic acid ethyl ester → 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butyric acid ethyl ester

Participants

Reaction Steps

4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-but-2-enoic acid ethyl ester (225 g, 0.9 mol) was dissolved in THF (700 mL) and treated with 5% Pd/C (17 g). The mixture was reduced by hydrogenation in a “Parr” shaker in a 2.5 L pressure bottle at 50 psi. The reaction was exothermic to 45° C. and was controlled by interrupting the shaking motion of the “Parr” shaker. The reaction was completed in approximately 2 hours. The reaction mixture was filtered through a 2-inch bed of the Solka Floc® reagent/magnesium sulfate to give a clear, colorless solution of the title compound (225 g in 1182 g of tetrahydrofuran, quantitative yield). Mass Spectrum (+ESI): 253 [M+H]+

Provenance & Evidence