Diethylsuccinoylsuccinate

Diethylsuccinoylsuccinate
Names
	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
CAS Number	16877-79-5;
3D model (JSmol)	Interactive image;
ChemSpider	10279533;
PubChem CID	54679331;
CompTox Dashboard (EPA)	DTXSID80715660;
	InChI Key: NSWNRIHCLWQMCD-UHFFFAOYSA-N; InChI=1S/C12H16O6/c1-3-17-11(15)7-5-10(14)8(6-9(7)13)12(16)18-4-2/h13-14H,3-6H2,1-2H3;
	SMILES CCOC(=O)C1=C(CC(=C(C1)O)C(=O)OCC)O;
Properties
Chemical formula	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).
	Infobox references

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]

2 EtO₂CCH₂CH₂CO₂Et [CH₂C(OH)=C(CO₂Et)]₂ + 2 EtOH

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]

References

Mez, Hans-Christian; Rihs, Gret (1973). "Chemistry of Succinylsuccinic Acid Derivatives. Part II. The crystal and molecular structure of diethyl succinylsuccinate". Helvetica Chimica Acta. 56 (8): 2766–2772. doi:10.1002/hlca.19730560812.
Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.
Hunger, K.; Herbst, W. (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371.(subscription required)
Smith, J. Anthony; West, Richard M.; Allen, Malcolm (2004). "Acridones and Quinacridones: Novel Fluorophores for Fluorescence Lifetime Studies". Journal of Fluorescence. 14 (2): 151–171. doi:10.1023/B:JOFL.0000016287.56322.eb.
Labana, S. S.; Labana, L. L. (1967). "Quinacridones". Chemical Reviews. 67: 1–18. doi:10.1021/cr60245a001.

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[1] Mez, Hans-Christian; Rihs, Gret (1973). "Chemistry of Succinylsuccinic Acid Derivatives. Part II. The crystal and molecular structure of diethyl succinylsuccinate". Helvetica Chimica Acta. 56 (8): 2766–2772. doi:10.1002/hlca.19730560812.

[OS-2] Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.

[Ullmann-3] Hunger, K.; Herbst, W. (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371.(subscription required)

[4] Smith, J. Anthony; West, Richard M.; Allen, Malcolm (2004). "Acridones and Quinacridones: Novel Fluorophores for Fluorescence Lifetime Studies". Journal of Fluorescence. 14 (2): 151–171. doi:10.1023/B:JOFL.0000016287.56322.eb.

[5] Labana, S. S.; Labana, L. L. (1967). "Quinacridones". Chemical Reviews. 67: 1–18. doi:10.1021/cr60245a001.