Oxygen → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-
Reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1[OH:4].CC1C=CC(O)=C(C)C=1C.CC1C(C)=CC(C)=CC=1O.CC1C(C)=CC=C(C)C=1O.O=O>CN(C)C=O.[Co]>[CH3:1][C:2]1[C:3](=[O:4])[CH:5]=[C:6]([CH3:11])[C:7](=[O:10])[C:8]=1[CH3:9]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
In the process for the preparation of 2,3,5-trimethylhydroquinone by (a) catalytic oxidation of a trimethylphenol starting material selected from the class consisting of 2,3,5-trimethylphenol, 2,3,6-trimethylphenol and mixtures thereof by reaction with oxygen in the presence of a cobalt chelate complex in a dimethylformamide solvent to afford 2,3,5-trimethyl-p-benzoquinone followed by (b) catalytic hydrogenation of the 2,3,5-trimethyl-p-benzoquinone thus formed by reaction with hydrogen in the presence of a noble metal catalyst, the improvement which comprises; (1) mixing the 2,3,5-trimethyl-p-benzoquinone containing reaction mixture from step (a) with di-n-butyl ether and water to form a di-n-butyl ether phase containing 2,3,5-trimethyl-p-benzoquinone, a precipitate comprising the cobalt catalyst and an aqueous phase containing the dimethylformamide reaction solvent, (2) separating the di-n-butyl ether phase from the precipitate and aqueous phase, and (3) subjecting the separated di-n-butyl ether phase to catalytic hydrogenation according to reaction step (b), said di-n-butyl ether functioning as the reaction solvent.
Sources & evidence
- ORD record
- ord-08af2e4525424eaa8966c587d376b36a
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04250335
Reaction notes
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