4,4-Diethylcyclohex-2-en-1-one → 4,4-Diethylcyclohexan-1-one

HRID 1934765Notes

Reaction equation

HRID 1934765 reaction equation
[CH2:1]([C:3]1([CH2:10][CH3:11])[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=[CH:4]1)[CH3:2].[H][H]>C(O)(=O)C.[C].[Pd]>[CH2:10]([C:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)[CH3:11]

Participants

5

Reactant 2

HCID 124849234,4-Diethylcyclohex-2-en-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 148363144,4-Diethylcyclohexan-1-oneYield 85.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

In 22 ml of acetic acid was dissolved 2.20 g of 4,4-diethyl-2-cyclohexen-1-one, to which was added 0.22 g of 5% palladium-carbon. Under a pressure of 5 atmospheres, the mixture was stirred at ambient temperature for one hour under a stream of hydrogen. The reaction mixture was filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluent: hexane:ethyl acetate=10:1] gave 1.90 g of 4,4-diethyl-1-cyclohexanone as a colorless oily product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe solvent was distilled off under reduced pressure
  3. customPurification of the residue by column chromatography [eluent: hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-37d295d9975e41e9a5391a690d72d181
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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