2,4-Di-tert-butylphenol → 3,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diol

HRID 964401Notes

Reaction equation

HRID 964401 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]>O>[C:11]([C:9]1[CH:8]=[C:7]([C:7]2[C:6]([OH:15])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:8]=2)[C:6]([OH:15])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 1

HCID 73112,4-Di-tert-butylphenol

Product 1

HCID 808083,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diolYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 24 g (0.1 mol) of 3,3',5,5'-tetramethyldipheno-4,4'-quinone obtained in Example 2 and 52 g (0.25 mol) of 2,4-di-t-butylphenol was boiled in 150 ml of water for 4 hours. The reaction mixture was filtered and dried. Formation of 2,2',6,6'-tetramethyl-4,4'-biphenol and 4,4',6,6'-tetra-t-butyl-2,2'-biphenol was confirmed by GPC and liquid chromatography. 20 g of pure 4,4',6,6'-tetra-t-butyl-2,2'-biphenol were isolated by extraction of hot isooctane and washing by methanol.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customdried

Sources & evidence

ORD record
ord-8c5a7d3563b047729cbad64409842ec9
Source dataset
uspto-grants-1998_06
Patent number
US05767327

Reaction notes

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