4-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one → 4-Hydroxy-4-(trifluoromethyl)cyclohexan-1-one

HRID 1382015Notes

Reaction equation

HRID 1382015 reaction equation
[OH:1][C:2]1([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:6][C:5](=[O:8])[CH:4]=[CH:3]1.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1([C:9]([F:10])([F:11])[F:12])[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 138691094-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 200351424-Hydroxy-4-(trifluoromethyl)cyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 100 mg of 4-hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one in 1 mL of absolute ethanol was treated with a few mg of 5% palladium on carbon, hydrogenated in a Parr shaker for one hour under 50 psig of hydrogen, and filtered. Gas chromatographic/mass spectral analysis indicated that the major component of the filtrate was 4-hydroxy-4-trifluoromethylcyclohexanone: mass spectrum (70 eV) m/z (relative intensity) 182 (11, M+), 55 (100), 42 (40).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-bf7d98fbd4fd4822bc446743af8607f8
Source dataset
uspto-grants-1989_02
Patent number
US04804773

Reaction notes

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