Names | |
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Preferred IUPAC name
Diethyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate | |
Other names
2,5-Dihydroxy-1,4-cyclohexadiene-1,4-dicarboxylic acid
1,4-Bis(ethoxycarbonyl)-2,5-dihydroxy-1,4-cyclohexadiene | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H16O6 | |
Molar mass | 256.254 g·mol−1 |
Appearance | white solid |
Density | 1.414 g/cm3 |
Melting point | 125–126 °C (257–259 °F; 398–399 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diethylsuccinoylsuccinate is an organic compound with the formula [CH2C(OH)=C(CO2Et)]2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione.[1] It is produced by base-induced condensation of diethyl succinate:[2]
Diethylsuccinylsuccinate is valued as a precursor to the quinacridone pigments. For example, it reacts with two equiv of anilines to give the diamines [CH2C(N(H)Ar)=C(CO2Et)]2, which undergoes cyclization upon treatment with acid to give dihydroquinacridone.[3][4][5]
When heated in the presence of acid, diethylsuccinoylsuccinate converts to 1,4-cyclohexanedione via hydrolysis of the esters followed by decarboxylation.[2]