119711-73-8

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 4-[(1,1-dimethylethyl)dioxy]-4-methyl-
• CAS NO: 119711-73-8
• Molecular Formula: C11H16O3
• Molecular Weight: 196.246
• Mol File: 119711-73-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 4-[(1,1-dimethylethyl)dioxy]-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 4-[(1,1-dimethylethyl)dioxy]-4-methyl-(119711-73-8)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 4-[(1,1-dimethylethyl)dioxy]-4-methyl-(119711-73-8)

Safety Data

• Hazardous Substances Data: 119711-73-8(Hazardous Substances Data)

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 106-44-5 p-cresol 
• 106-49-0 p-toluidine 
• 142260-70-6 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one 
• 52457-01-9 3-Methylcyclohexa-1,4-diene-3-carboxylic acid 

Downstream Products

• 58-27-5 menadione 
• 84-80-0 phytomenadione 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 24456-96-0 2-tert-butyl-5-methyl-1,4-benzoquinone 

Relevant articles and documents

Synthesis of 2-substituted quinones, vitamin K3, and vitamin K1 from p-cresol. BF3·OEt2-catalyzed methyl migration of 4-tert-butyldioxycyclohexadienones

BF3·OEt2-catalyzed methyl group migration of 4-methyl-4-tert-butyldioxycyclohexadienone, which is obtained by ruthenium-catalyzed oxidation of p-cresol with tert-butyl hydroperoxide, in hexafluoro-2-propanol/toluene gave toluquinone efficiently. The reaction can be applied to the regio-selective short-step syntheses of vitamin K3 and vitamin K1 from p-cresol.

Ruthenium-catalyzed oxidation of phenols with alkyl hydroperoxides. A novel, facile route to 2-substituted quinones

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Dirhodium-catalyzed phenol and aniline oxidations with T-HYDRO. Substrate scope and mechanism of oxidation

Dirhodium caprolactamate, Rh2(cap)4, is a very efficient catalyst for the generation of the tert-butylperoxy radical from tert-butyl hydroperoxide, and the tert-butylperoxy radical is a highly effective oxidant for phenols and anilines. These reactions are performed with 70% aqueous tert-butyl hydroperoxide using dirhodium caprolactamate in amounts as low as 0.01 mol % to oxidize para-substituted phenols to 4-(tert-butyldioxy) cyclohexadienones. Although these transformations have normally been performed in halocarbon solvents, there is a significant rate enhancement when Rh 2(cap)4-catalyzed phenol oxidations are performed in toluene or chlorobenzene. Electron-rich and electron-poor phenolic substrates undergo selective oxidation in good to excellent yields, but steric influences from bulky para substituents force oxidation onto the ortho position resulting in ortho-quinones. Comparative results with RuCl2(PPh 3)3 and CuI are provided, and mechanistic comparisons are made between these catalysts that are based on diastereoselectivity (reactions with estrone), regioselectivity (reactions with p-tert-butylphenol), and chemoselectivity in the formation of 4-(tert-butyldioxy)cyclohexadienones. The data obtained are consistent with hydrogen atom abstraction by the tert-butylperoxy radical followed by radical combination between the phenoxy radical and the tert-butylperoxy radical. Under similar reaction conditions, para-substituted anilines are oxidized to nitroarenes in good yield, presumably through the corresponding nitrosoarene, and primary amines are oxidized to carbonyl compounds by TBHP in the presence of catalytic amounts of Rh 2(cap)4.

Free-radical oxidation of para-substituted phenols by hypervalent tert-butylperoxiodane and tert-butyl hydroperoxide: Synthesis of 4-(tert-butylperoxy)-2,5-cyclohexadien-1-ones

Oxidation of 4-alkylphenols 1 by 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one (2) in the presence of tert-butyl hydroperoxide affords selectively 4-(tert-butylperoxy)-2,5-cyclohexadien-1-ones 3 in good yields. Evidence for the involvement of free-radicals is reported.