Tert-Butylhydroquinone → tert-Butyl-1,4-benzoquinone

HRID 1733184Notes

Reaction equation

HRID 1733184 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].S([O-])([O-])(=O)=O.[Na+].[Na+]>[Ag]=O.CCOCC>[C:1]([C:5]1[C:6](=[O:7])[CH:8]=[CH:9][C:10](=[O:12])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 16043Tert-ButylhydroquinoneHCID 24436Sodium Sulfate

Product 1

HCID 19211tert-Butyl-1,4-benzoquinone

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55°-60° C.

Workup

  1. additionTo this mixture was added 60 g
  2. customAn exothermic reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate evaporated under the hood

Sources & evidence

ORD record
ord-1e063470625443a6993b7446fc66aa0a
Source dataset
uspto-grants-1980_12
Patent number
US04240974

Reaction notes

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