trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-5-methylcyclohexanone → trans-3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-5-methyl-cyclohexanone

HRID 1074486Notes

Reaction equation

HRID 1074486 reaction equation
C([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[C@H:24]1[CH2:29][C@H:28]([CH3:30])[CH2:27][C:26](=[O:31])[CH2:25]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH3:23][C:15]([C:13]1[CH:12]=[CH:11][C:10]([C@H:24]2[CH2:29][C@H:28]([CH3:30])[CH2:27][C:26](=[O:31])[CH2:25]2)=[C:9]([OH:8])[CH:14]=1)([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 70529131trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-5-methylcyclohexanoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 70530367trans-3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-5-methyl-cyclohexanoneYield 64.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-5-methylcyclohexanone (175 mg, 0.417 mmole) and 175 mg of 5% palladium on carbon-50% water in methanol (8 ml) was stirred under one atmosphere of hydrogen gas until hydrogen uptake ceased. The reaction mixture was filtered through diatomaceous earth and the filtrate evaporated under reduced pressure. Crystallization of the residue in pentane gave 89 mg (64%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate evaporated under reduced pressure
  3. customCrystallization of the residue in pentane

Sources & evidence

ORD record
ord-a86551ca10db44bbbfcba6a643d974da
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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