Diethylsuccinoylsuccinate is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula H₂C(OH)=C(CO₂Et)sub>2 (Et =

ethyl Ethyl may refer to: Arts and entertainment * Cold Ethyl, a Swedish rock band *Ethyl Sinclair, a character in the ''Dinosaurs'' television show Science and technology * Ethyl group, an organic chemistry moiety * Ethyl alcohol (or ethanol) * E ...

). A tetrasubstituted derivative of

1,4-cyclohexadiene 1,4-Cyclohexadiene is an organic compound with the formula C6H8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an example being γ-terpinene. An isomer of ...

, the compound is the

enol In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The te ...

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...

of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate: :2 EtO₂CCH₂CH₂CO₂Et H₂C(OH)=C(CO₂Et)sub>2 + 2 EtOH Diethylsuccinylsuccinate is valued as a precursor to the

quinacridone Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, ...

pigments. For example, it reacts with two equiv of

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

s to give the diamines H₂C(N(H)Ar)=C(CO₂Et)sub>2, which undergoes cyclization upon treatment with acid to give dihydroquinacridone. When heated in the presence of acid, diethylsuccinoylsuccinate converts to 1,4-cyclohexanedione via hydrolysis of the esters followed by decarboxylation.{{cite journal, doi=10.15227/orgsyn.045.0025, title=1,4-Cyclohexanedione, journal=Organic Syntheses, first1=Arnold T., last1=Nielsen, first2=Wayne R., last2=Carpenter, volume=45, pages=25, year=1965

References

Cyclohexadienes