Hydrogen Peroxide → 3,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diol

HRID 1702230Notes

Reaction equation

HRID 1702230 reaction equation
[OH-:1].[Na+].[C:3]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].OO>O.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+]>[OH:17][C:8]1[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])=[CH:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][C:9]=1[C:9]1[CH:8]=[C:7]([C:3]([CH3:5])([CH3:4])[CH3:6])[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[OH:1]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 73112,4-Di-tert-butylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 808083,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diolYield 98%

Reagents, catalysts & solvents 2

HCID 3423265Sodium Lauryl SulfateCatalystHCID 962WaterSolvent

Procedure

40 g (1 mole) of sodium hydroxide are dissolved in 170 ml of water which contains 1 g of sodium lauryl sulfate. With stirring, the solution is heated to 80° and then 103 g (0.5 mole) of 2,4-di-tert-butylphenol are added. Then 31 ml of a 30% solution of hydrogen peroxide are added dropwise in the course of 2 hours. After the reaction mixture has cooled, the product is isolated by filtration and washed with water and dried, affording 100.5 g (98% of theory) of 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butyl-biphenyl with a melting point of 190°-195° C.

Workup

  1. temperaturethe solution is heated to 80°
  2. temperatureAfter the reaction mixture has cooled
  3. customthe product is isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4d1d82f1663f4efbb148f80c2cf161ee
Source dataset
uspto-grants-1983_04
Patent number
US04380676

Reaction notes

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