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Diethylsuccinoylsuccinate

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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
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Appearance white solid
Density 1.414 g/cm
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 , 100 kPa). Infobox references
Chemical compound

Diethylsuccinoylsuccinate is an organic compound with the formula 2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate:

2 EtO2CCH2CH2CO2Et 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 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.

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. ISBN 978-3527306732.(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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