Diethyl phenylmalonate

Diethyl phenylmalonate is an aromatic malonic ester used in the synthesis of moderate to long lasting barbiturates such as phenobarbital.[1]

Diethyl phenylmalonate
Diethyl phenylmalonate
Names
IUPAC name
Diethyl phenylmalonate
Other names
Diethyl phenylpropanedioate; Propanedioic acid 2-phenyl- diethyl ester; Diethyl-phenylmalonat
Identifiers
3D model (JSmol)
614465
ChemSpider
ECHA InfoCard 100.001.324
EC Number
  • 201-456-5
UNII
  • InChI=1S/C13H16O4/c1-3-16-12(14)11(13(15)17-4-2)10-8-6-5-7-9-10/h5-9,11H,3-4H2,1-2H3 checkY
    Key: FGYDHYCFHBSNPE-UHFFFAOYSA-N checkY
  • CCOC(=O)C(C1=CC=CC=C1)C(=O)OCC
Properties
C13H16O4
Molar mass 236.267 g·mol−1
Density 1.096 g/cm3
Melting point 16.5 °C (61.7 °F; 289.6 K)
Boiling point 170–172 °C (338–342 °F; 443–445 K) (14 mmHg)
n20/D 1.491
Hazards
Flash point 120
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chemical synthesis

Unlike other malonic esters that are derived via malonic ester synthesis, diethyl phenylmalonate is typically indirectly derived via a Claisen condensation with diethyl oxalate and ethyl phenylacetate followed by decarbonylation.[2] This indirect method is often used because aryl halides are relatively weaker electrophiles than alkyl halides and thus poorly alkylate diethyl malonate.[3] Methods using Caesium carbonate and copper(I) iodide have been developed to overcome this difficulty however.[4]

References
  1. Wollweber, Hartmund (2000). "Hypnotics". Ullmann's Encyclopedia of Industrial Chemistry: 11. doi:10.1002/14356007.a13_533. ISBN 3527306730.
  2. Meyer, G. M.; Levene, P. A. (1936). "Diethyl phenylmalonate". Organic Syntheses. 16: 33. doi:10.15227/orgsyn.016.0033.
  3. Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp. 1174–1179. ISBN 9780582462366.
  4. Hennessy, Edward J.; Buchwald, Stephen L. (2002). "A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate". Organic Letters. 4 (2): 269–272. doi:10.1021/ol017038g. PMID 11796067.
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