2-Cyclohexen-1-one, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)- → Cyclohexanone, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-

HRID 1388633Notes

Reaction equation

HRID 1388633 reaction equation
[CH3:1][C:2]1[CH:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]([CH3:13])[CH2:5][C:4](=[O:14])[CH:3]=1.[H][H]>[OH-].[K+].[Pd]>[CH3:1][CH:2]1[CH:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]([CH3:13])[CH2:5][C:4](=[O:14])[CH2:3]1

Participants

5

Reactant 2

HCID 936962-Cyclohexen-1-one, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 20469263Cyclohexanone, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-Yield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 3,5-dimethyl-4-(3-methyl-2-butenyl)-2-cyclohexen-1-one (8.2 g, 0.043 mol) in 0.3 M ethanolic KOH (16 mL) was hydrogenated at room temperature and 1 atmosphere over 5% palladium on carbon (0.8 g). After uptake of 1 equivalent of hydrogen, the solution was filtered through Celite and concentrated. The residue was partitioned between hexane and water; then the hexane layer was dried (Na2SO4) and the solvent removed on a rotary evaporator. Kugelrohr distillation gave 7.3 g of 3,5-dimethyl-4-(3-methyl-2-butenyl) cyclohexanone, bp 115° C./0.5 mm.

Workup

  1. customwas hydrogenated at room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between hexane and water
  4. dry with materialthen the hexane layer was dried (Na2SO4)
  5. customthe solvent removed on a rotary evaporator
  6. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-673dae9503fe48e9a3f3a48cc694016f
Source dataset
uspto-grants-1984_02
Patent number
US04432378

Reaction notes

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