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

HRID 67152

Reaction equation

HRID 67152 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]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[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

4

Reactant 1

HCID 16043Tert-Butylhydroquinone

Product 1

HCID 19211tert-Butyl-1,4-benzoquinoneYield 80%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

16.6 g (0.10 mol) of 2-tert-butylhydroquinone was placed in a 200 cc 3-neck flask. After adding 17.4 g (0.20 mol) of powdery manganese dioxide, 100 cc of toluene was added thereto, and the mixture was heated with stirring. The temperature was maintained at 70° C. for 3 hours. After cooling to room temperature, the manganese dioxide was removed by filtration by means of suction using Celite as a filter aid. Then the manganese dioxide was washed with 50 cc of toluene, and the toluene was evaporated to dryness, by which 2-tert-butyl-1,4-benzoquinone was obtained. The yield was 80% and the melting point was 48°-50° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe manganese dioxide was removed by filtration by means of suction
  5. washThen the manganese dioxide was washed with 50 cc of toluene
  6. customthe toluene was evaporated to dryness, by which 2-tert-butyl-1,4-benzoquinone
  7. customwas obtained

Sources & evidence

ORD record
ord-5837863e67dc4d6886cf275d938e21dc
Source dataset
uspto-grants-1982_08
Patent number
US04345016

Linked notes

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