Cumene → 2-Phenyl-2-propanol

HRID 2085613Notes

Reaction equation

HRID 2085613 reaction equation
[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:10]N1C(=O)C2=CC=CC=C2C1=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])[CH3:9].[C:1]1([C:7]([OH:10])([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 2

HCID 7406CumeneHCID 10665N-Hydroxyphthalimide

Product 4

HCID 996PhenolYield 10.4%HCID 7406CumeneHCID 7410AcetophenoneHCID 120532-Phenyl-2-propanolYield 13.1%

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Procedure

In a round-bottom flask fitted with superposed reflux condenser, 30 mmol of cumene are admixed at a temperature of 125° C. with 0.3 mmol of N-hydroxyphthalimide and 0.3 mmol of cobalt(II) acetate. The reaction mixture is stirred at the specified temperature under an oxygen atmosphere of 1 bar for 8 hours. The target product is not formed, but instead acetophenone with a selectivity of 58.7%, 2-phenyl-2-propanol (13.1%) and phenol (10.4%) are obtained at a cumene conversion of 49.3%.

Workup

  1. customIn a round-bottom flask fitted with superposed reflux condenser
  2. customThe target product is not formed

Sources & evidence

ORD record
ord-8e80c8018ef1491b989bf2bd04177786
Source dataset
uspto-grants-2004_04
Patent number
US06720462B2

Reaction notes

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