1-Benzyloxy-4-(3,3-dimethyl-cyclohex-1-enyl)-benzene → 4-(3,3-Dimethyl-cyclohexyl)-phenol

HRID 237760Notes

Reaction equation

HRID 237760 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:20][CH2:19][CH2:18][C:17]([CH3:22])([CH3:21])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH3:21][C:17]1([CH3:22])[CH2:18][CH2:19][CH2:20][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:16]1

Participants

5

Reactant 1

HCID 685247081-Benzyloxy-4-(3,3-dimethyl-cyclohex-1-enyl)-benzene

Product 1

HCID 685291054-(3,3-Dimethyl-cyclohexyl)-phenolYield 102.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-benzyloxy-4-(3,3-dimethyl-cyclohex-1-enyl)-benzene (4.3 g, 16.4 mmol) in MeOH (50 mL) and EtOAc (50 mL) was added 10% Pd/C (0.67 g) under N2. This mixture was stirred under H2 (1 atm) overnight. The reaction mixture was filtered through celite. The filtrate was concentrated to give the title compound as a white solid (3.43 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7dfa238d8d274833ae53a7002e2ed873
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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