Diethylsuccinoylsuccinate

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
Diethylsuccinoylsuccinate
Names
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)
ChemSpider
UNII
  • 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
  • CCOC(=O)C1=C(CC(=C(C1)O)C(=O)OCC)O
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).
Infobox references

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