5-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-methyl-2-cyclohexen-1-one → cis-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-5-methyl-cyclohexanone

HRID 1074484Notes

Reaction equation

HRID 1074484 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=[O:30])[CH:27]=[C:26]([CH3:31])[CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:25][C@@H:26]([CH3:31])[CH2:27][C:28](=[O:30])[CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 127882945-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-methyl-2-cyclohexen-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 70529864cis-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-5-methyl-cyclohexanoneYield 32.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-methyl-2-cyclohexen-1-one (1.00 g, 2.39 mmole) and 500 mg of 5% palladium on carbon-50% water was stirred under one atmosphere of hydrogen for one hour. A second 500 mg portion of catalyst was added and stirring continued for 30 minutes. A third 500 mg portion of catalyst was added and stirring continued for 13 minutes. The reaction mixture was then filtered through sodium bicarbonate and magnesium sulfate and the filtrate evaporated. The residue was purified via column chromatography on 140 g of silica gel eluted with 10% ether-petroleum ether to yield 323 mg (32%) of the title compound as an oil.

Workup

  1. additionA second 500 mg portion of catalyst was added
  2. stirringstirring
  3. waitcontinued for 13 minutes
  4. filtrationThe reaction mixture was then filtered through sodium bicarbonate and magnesium sulfate
  5. customthe filtrate evaporated
  6. customThe residue was purified via column chromatography on 140 g of silica gel
  7. washeluted with 10% ether-petroleum ether

Sources & evidence

ORD record
ord-9f4eba4642fa44618ca58e1ebc90d666
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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