Ethyl 4-(trifluoromethyl)benzoate → Ethyl 4-(trifluoromethyl)cyclohexane-1-carboxylate

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.[H][H]>C(O)C.[Rh]>[F:1][C:2]([F:14])([F:15])[CH:3]1[CH2:4][CH2:5][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:12][CH2:13]1

Participants

Procedure

Ethyl 4-trifluoromethylbenzoate (4.9 g) was dissolved in ethanol (60 ml) and catalyst (5% rhodium on alumina, 0.5 g) added. Reduction with hydrogen gas was effected at ambient temperature at 50 atmospheres pressure until the theoretical quantity of hydrogen had been absorbed. The catalyst was removed by filtration through "hyflo" filter aid and the solvent was removed by evaporation to provide crude ethyl 4-trifluoromethylcyclohexane-1-carboxylate.