Oxygen → 2,3,6-Trimethylphenol
Reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[CH:4]([CH3:9])[CH:5]([CH3:8])[CH2:6][CH:7]=1.O=O>[Cu]=O>[CH3:9][C:4]1[C:5]([CH3:8])=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[OH:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
If the reaction mixture comprising 2,5,6-trimethylcyclohex-2-en- 1-one, alkanol, the catalytic amount of copper oxide and hydrogen halide gas, as described above, is allowed to react for a longer time with air or oxygen, 4-halo-2,3,6-trimethylphenol is obtained in addition to 2,3,6-trimethylphenol. If, instead of isolating this product, the reaction mixture is treated, as described above, with an alkali metal alcoholate, and the oxidation with air or oxygen is continued, the 4-halo-2,3,6-trimethylphenol is also converted to 2,3,5-trimethyl-p-benozoquinone. After the reaction products obtained in step A have been treated with an alkali metal alcoholate, they can also be oxidized with tert.-butyl hydroperoxide instead of air or oxygen. Depending on whether trimethylphenol or halotrimethylphenol is the predominant product, subsequent oxidation with tert.-butyl hydroperoxide gives 2,3,5-trimethyl-p-benzoquinone in a yield of from 65 to 80% of theory.
Sources & evidence
- ORD record
- ord-e434c6e789d44788be3a1e02232a1de6
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04491545
Reaction notes
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