3-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enone → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone

HRID 1074474Notes

Reaction equation

HRID 1074474 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:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=1)C1C=CC=CC=1.[H][H]>[Pd]>[CH3:23][C:15]([C:13]1[CH:12]=[CH:11][C:10]([C:24]2[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=2)=[C:9]([OH:8])[CH:14]=1)([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 198553803-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 127882083-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenoneYield 35%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 400 mg. (0.988 mmole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-2-enone and 20 mg. of 5% palladium-on-carbon was stirred under one atmosphere of hydrogen pressure for 30 minutes. The reaction mixture was then filtered through diatomaceous earth with ether and the filtrate evaporated to a solid. The crude solid was recrystallized from petroleum ether to yield 110 mg. (35%) of the title compound, M.P. 122°-123° C.

Workup

  1. additionA mixture of 400 mg
  2. filtrationThe reaction mixture was then filtered through diatomaceous earth with ether
  3. customthe filtrate evaporated to a solid
  4. customThe crude solid was recrystallized from petroleum ether
  5. customto yield 110 mg

Sources & evidence

ORD record
ord-d6923f60226b49afac01b3d45df8a73f
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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