5-(3,4-Dimethoxyphenyl)-2-cyclohexen-1-one → 3-(3,4-Dimethoxyphenyl)cyclohexanone

HRID 1108757Notes

Reaction equation

HRID 1108757 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][C:15](=[O:17])[CH:14]=[CH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H][H].Cl.C(OCC)(=O)C>C(O)C.C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:12][CH2:13][CH2:14][C:15](=[O:17])[CH2:16]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 3

HCID 187841395-(3,4-Dimethoxyphenyl)-2-cyclohexen-1-oneHCID 21866389Hydrogen chloride-ethyl acetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 187841823-(3,4-Dimethoxyphenyl)cyclohexanoneYield 98.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(3,4-Dimethoxyphenyl)-2-cyclohexen-1-one (6.76 g) was dissolved in ethanol (100 ml), and 10% palladium-carbon (684 mg) was added thereto. After substituting the reaction vessel with hydrogen gas, hydrogen addition was effected for 30 minutes at normal pressure and room temperature. After the reaction, the catalyst was filtered off and the solvent was distilled off under reduced pressure to produce an oily substance which was dissolved in ethyl acetate (50 ml), and then 4 N HCl-ethyl acetate solution (2 ml) was added and the mixture was stirred at room temperature for 20 minutes. The solvent was distilled off under reduced pressure to produce crude crystals which were then washed with n-hexane to give 6.72 g of 3-(3,4-dimethoxyphenyl)cyclohexanone (98.5%).

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto produce an oily substance which
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto produce crude crystals which
  7. washwere then washed with n-hexane

Sources & evidence

ORD record
ord-d3b8805eb9db490385840eebd55aeaee
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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