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

HRID 1682180Notes

Reaction equation

HRID 1682180 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

5

Reactant 2

HCID 521827Ethyl 4-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22182861Ethyl 4-(trifluoromethyl)cyclohexane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

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.

Workup

  1. customhad been absorbed
  2. customThe catalyst was removed by filtration through "hyflo"
  3. filtrationfilter aid
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-87d9f1fa6db14214b4adae390ad67c99
Source dataset
uspto-grants-1992_12
Patent number
US05175319

Reaction notes

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