1-Benzyloxy-4-(3,3,5,5-tetramethyl-cyclohex-1-enyl)-benzene → 4-(3,3,5,5-Tetramethyl-cyclohexyl)-phenol

HRID 237811Notes

Reaction equation

HRID 237811 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]([CH3:24])([CH3:23])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH3:23][C:17]1([CH3:24])[CH2:18][C:19]([CH3:21])([CH3:22])[CH2:20][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:16]1

Participants

5

Reactant 1

HCID 685258151-Benzyloxy-4-(3,3,5,5-tetramethyl-cyclohex-1-enyl)-benzene

Product 1

HCID 685258634-(3,3,5,5-Tetramethyl-cyclohexyl)-phenolYield 96.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10% Pd/C (0.17 g) under N2 was added 1-benzyloxy-4-(3,3,5,5-tetramethyl-cyclohex-1-enyl)-benzene (1.7 g, 5.3 mmol), prepared by a substantially similar procedure to that of Step 1 of Example 18, in MeOH (15 mL) and EtOAc (15 mL). 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 (1.19 g).

Workup

  1. customprepared by a substantially similar procedure to that of Step 1 of Example 18
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8b5b782ad61043aab7f5d69373edc6f7
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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