Diethyl phenylmalonate

Diethyl phenylmalonate

Names
IUPAC name Diethyl phenylmalonate
Other names Diethyl phenylpropanedioate; Propanedioic acid 2-phenyl- diethyl ester; Diethyl-phenylmalonat
Identifiers
CAS Number	83-13-6
3D model (Jmol)	Interactive image
Beilstein Reference	614465
ChemSpider	59885
ECHA InfoCard	100.001.324
EC Number	201-456-5
PubChem	66514
InChI 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 Key: FGYDHYCFHBSNPE-UHFFFAOYSA-N
SMILES CCOC(=O)C(C1=CC=CC=C1)C(=O)OCC
Properties
Chemical formula	C13H16O4
Molar mass	236.27 g·mol^−1
Density	1.096 g/cm^3
Melting point	16.5 °C (61.7 °F; 289.6 K)
Boiling point	170–172 °C (338–342 °F; 443–445 K) (14 mmHg)
Refractive index (nD)	n20/D 1.491
Hazards
Safety data sheet	MSDS
Flash point	120
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

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 nucleophiles than aliphatic halocarbons 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.
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.