4-tert-Butylphenol → 4-tert-Butylcyclohexanol

HRID 2174256Notes

Reaction equation

HRID 2174256 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Rh].C(O)C>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([OH:11])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 73934-tert-Butylphenol

Product 1

HCID 73914-tert-ButylcyclohexanolYield 87.5%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

U.S. Pat. No. 2,927,127 discloses that hydrogenation of p-tert-butyl phenol with a Ni catalyst yields p-tert-butyl cyclohexanol having proportions of approximately 30% cis-isomer and approximately 70% trans-isomer. U.S. Pat. No. 2,927,127 further describes the hydrogenation of p-tert-butyl phenol using Rh/C as catalyst in ethanol to yield p-tert-butyl cyclohexanol containing 87.5% of the cis-isomer, which was subsequently converted to the corresponding acetates by reaction with acetic anhydride.

Sources & evidence

ORD record
ord-3aba8a21d3834db593c41c4989e6843d
Source dataset
uspto-grants-2015_06
Patent number
US09060943B2

Reaction notes

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