Hydrogen Bromide → 2,6-Di-tert-butylhydroquinone

HRID 1682173Notes

Reaction equation

HRID 1682173 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH:16]O.Br>CO>[C:11]([C:7]1[CH:8]=[C:9]([OH:16])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 755502,6-Di-tert-butylhydroquinoneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,6-di-tert.butyl-phenol (11 g, 53.3 mmol), hydrogen peroxide at 60% (8 ml) and hydrogen bromide (5 g, 61.7 mmol) in methanol (150 ml) is refluxed for 25 minutes. On concentrating the solution, 2,6-di-tert.butyl-1,4-benzoquinone (10.5 g, 89.4%) crystallizes. This product is hydrogenated, in methanol (110 ml), in autoclave, with Pd/C at 5% (0.12 g), under a hydrogen pressure of 10 kg/cm2, for 50 minutes, at 20° C. After the catalyst being filtered off, and solvent evaporation, 2,6-di-tert.butyl-hydroquinone is obtained with a yield of 97%.

Workup

  1. concentrationOn concentrating the solution, 2,6-di-tert.butyl-1,4-benzoquinone (10.5 g, 89.4%)
  2. customcrystallizes
  3. customat 20° C
  4. filtrationAfter the catalyst being filtered off
  5. customsolvent evaporation

Sources & evidence

ORD record
ord-e1a20fabb34144868ec319ecf994bce7
Source dataset
uspto-grants-1992_12
Patent number
US05175318

Reaction notes

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