Benzene → 2,4,6-Trimethylphenol

HRID 2219984Notes

Reaction equation

HRID 2219984 reaction equation
C1C=CC=CC=1.[C:7]1([CH3:15])[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[CH:8]=1.O=O.C1(C2C=CC=CC=2)C=CC=CC=1.CC1C=C(C)C=C(C)C=1C1C=CC=CC=1.CC1C=C(C)C=C(C)C=1CC1C=C(C)C=C(C)C=1.C1([OH:69])C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[CH3:15][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[OH:69]

Participants

10

Reactant 7

HCID 241BenzeneHCID 977OxygenHCID 996PhenolHCID 7095BiphenylHCID 7947MesityleneHCID 198762,4,6-TrimethylbiphenylHCID 10125229Stk331795

Product 1

HCID 106982,4,6-TrimethylphenolYield 50%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

In a flask, 1.17 g (15 mmol) of benzene, 1.38 g (11 mmol) of mesitylene, 4.5 mg (0.02 mmol) of palladium(II) acetate, 323 mg (about 0.14 mmol) of H4PMo11V1O40-nH2O, and 10 ml of acetic acid were placed and were stirred at a constant temperature of 90° C. in an atmosphere of oxygen gas at 1 atm (0.1 MPa) for 15 hours. The resulting reaction mixture was analyzed by gas chromatography to find that 0.59 g (3.8 mmol) of biphenyl, 0.82 g (4.2 mmol) of 1,3,5-trimethyl-2-phenylbenzene, 0.85 g (3.6 mmol) of 1,3,5-trimethyl-2-(3′,5′-dimethylbenzyl)benzene, 0.13 g (1.4 mmol) of phenol, and 0.10 g (0.7 mmol) of 2,4,6-trimethylphenol were produced.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-1541eac1aa384f5fb243b8de672f21cb
Source dataset
uspto-grants-2008_08
Patent number
US07414160B2

Reaction notes

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