3-(4-Methoxyphenyl)-2-cyclohexen-1-one → 3-(4-Methoxyphenyl)cyclohexanone

HRID 2099939Notes

Reaction equation

HRID 2099939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=2)=[CH:5][CH:4]=1.[H][H].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>CO.ClCCl.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10]2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 3679273-(4-Methoxyphenyl)-2-cyclohexen-1-oneHCID 2724130Cornforth reagentHCID 9813011pyridine TFAHCID 178418361HCID 178418361, compound

Product 1

HCID 119770503-(4-Methoxyphenyl)cyclohexanone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g of 5% palladium on active carbon are added to 15.15 g of 3-(4-methoxyphenyl)-2-cyclohexen-1-one in 400 ml of methanol and stirring is carried out in a hydrogen atmosphere for 4 hours. The catalyst is filtered off and the reaction mixture is concentrated. The mixture so obtained is dissolved in 200 ml of dichloromethane and stirred with 26.9 g of pyridinium dichromate and 2.1 g of pyridinium trifluoroacetate at room temperature for 6 hours. The reaction mixture is decanted, concentrated and purified over silica gel. 3-(4-Methoxyphenyl)cyclohexanone is obtained in the form of a colourless oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe reaction mixture is concentrated
  3. customThe mixture so obtained
  4. customThe reaction mixture is decanted
  5. concentrationconcentrated
  6. custompurified over silica gel

Sources & evidence

ORD record
ord-b93427b7031f42fe9a2722fa8891c463
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

Loading…