O-Cresol → Methyl-1,4-benzoquinone

HRID 985745

Reaction equation

HRID 985745 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:9]O>C(O)(=O)C>[CH3:8][C:1]1[C:6](=[O:7])[CH:5]=[CH:4][C:3](=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 335O-CresolHCID 784Hydrogen Peroxide

Product 1

HCID 11122Methyl-1,4-benzoquinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of o-cresol (5 mmol) and Ti-superoxide catalyst (125 mg, 20% w/w) in acetic acid (5 ml) was heated with stirring at 50-60° C. under inert atmosphere. To this reaction mixture was added aq. 30% H2O2 (20 mmol) drop wise over 15 min. and heated for 1 h. The catalyst was recovered by simple filtration and 2-methyl-1,4-benzoquinone formed (96%) was separated by chromatographic purification.

Workup

  1. temperaturewas heated
  2. temperatureheated for 1 h
  3. filtrationThe catalyst was recovered by simple filtration and 2-methyl-1,4-benzoquinone
  4. customformed (96%)
  5. customwas separated by chromatographic purification

Sources & evidence

ORD record
ord-a408035d1b3342749cb9d480529dbc18
Source dataset
uspto-grants-2005_03
Patent number
US06872857B1

Linked notes

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