81453-27-2

Basic information

• Product Name: 4,4-diethoxy-2,5-cyclohexadien-1-one
• Synonyms: 4,4-diethoxy-2,5-cyclohexadien-1-one
• CAS NO: 81453-27-2
• Molecular Weight: 182.219
• Mol File: 81453-27-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4,4-diethoxy-2,5-cyclohexadien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-diethoxy-2,5-cyclohexadien-1-one(81453-27-2)
• EPA Substance Registry System: 4,4-diethoxy-2,5-cyclohexadien-1-one(81453-27-2)

Safety Data

• Hazardous Substances Data: 81453-27-2(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 1205-91-0 benzene-1,4-diyl diacetate 
• 72205-84-6 1,1,4,4-Tetraethoxy-1,4-dihydrobenzene 
• 622-62-8 4-Ethoxyphenol 
• 108-95-2 phenol 

Downstream Products

• 243975-17-9 5-ethyl-4,4-diethoxy-2-cyclohexenone 
• 243975-17-9 5-ethyl-4,4-diethoxy-2-cyclohexenone 
• 1446411-69-3 7-benzyl-8,8-diethoxy-6-oxa-7-azabicyclo[3.2.1]octan-3-one 
• 156-43-4 4-Ethoxyaniline 
• 1431660-62-6 C₁₆H₁₅NO 

Relevant articles and documents

Iodobenzene and m-chloroperbenzoic acid mediated oxidative dearomatization of phenols

Oxidative dearomatization of 2- and 4-substituted phenols to their corresponding benzoquinone monoketals by catalytic amount of iodobenzene, and m-CPBA as a co-oxidant has been achieved via in situ generation of PhIO2, a hypervalent iodine(V) s

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

A Mechanistic Study of the Thermal Disproportionation Reaction of Quinone Monoketals

Thermolysis of quinone monoketals 1a-d at 180 deg C leads to disproportionation to the p-alkoxyphenols 2a-d and the carbonyl compounds derived from the alcohol moiety of the ketal.The thermolysis of 4,4-dimethoxy-2,5-cyclohexadienone (1a) followed first-order kinetics, and the rate of reaction decreased by a factor of 3.6 when the methoxy groups were replaced with methoxy-d3 groups.The suggested mechanism for the reaction involves reversible dissociation of 1a into a p-methoxyphenoxy-methoxy radical pair, followed by rate-controlling hydrogen atom transfer to give p-methoxyphenol and formaldehyde.Although 1a has a half-life of about 4 h at 180 deg C, the monoethylene glycol ketal of benzoquinone was recovered in > 90percent yield after heating for 24 h at the same temperature.Finally, acid-catalysed exchange of 3,3,6,6-tetramethoxy-1,4-cyclohexadiene with alcohols furnished a convenient route to quinone bisketals not obtainable in good yield via anodic oxidation.