O-Cresol → Methyl-1,4-benzoquinone
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureheated for 1 h
- filtrationThe catalyst was recovered by simple filtration and 2-methyl-1,4-benzoquinone
- customformed (96%)
- customwas separated by chromatographic purification
Sources & evidence
- ORD record
- ord-a408035d1b3342749cb9d480529dbc18
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06872857B1
Reaction notes
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