Phenol → 3,4-Dimethylphenol

HRID 1699512Notes

Reaction equation

HRID 1699512 reaction equation
[CH3:1][C:2]1[C:3]([CH3:9])=[C:4](O)[CH:5]=[CH:6][CH:7]=1.C1([OH:16])C=CC=CC=1.CC(=C)C.C1(O)C(C2C(O)=CC=CC=2)=CC=CC=1.[Cr]([O-])([O-])(=O)=O.[K+].[K+]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([OH:16])[CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 5

HCID 996PhenolHCID 8255IsobutyleneHCID 106872,3-DimethylphenolHCID 15731(1,1'-Biphenyl)-2,2'-diolHCID 24597Potassium chromate(VI)

Product 1

HCID 72493,4-Dimethylphenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

dimethylphenol in two steps. The phenol was alkylated at 65° C. under 2 atmospheres of isobutylene and a catalytic amount of suilfric acid. The crude trialkylphenol was oxidized directly to the biphenol with potassium chromate in hot acetic acid. The overall yield from 3,4-dimethyl phenol was ˜50%.

Sources & evidence

ORD record
ord-ee0f7d4bad7348fea309f2577d727e41
Source dataset
uspto-grants-2002_02
Patent number
US06346652B1

Reaction notes

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