Diethyl(phenylacetyl)malonate Chemical Properties

Boiling point:

120 °C(Press: 0.01 Torr)

Density 

1.148±0.06 g/cm3(Predicted)

pka

8.76±0.59(Predicted)

form 

Brown liquid

InChI

InChI=1S/C15H18O5/c1-3-19-14(17)13(15(18)20-4-2)12(16)10-11-8-6-5-7-9-11/h5-9,13H,3-4,10H2,1-2H3

InChIKey

ZASPDQDIPTZTQQ-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(C(CC1=CC=CC=C1)=O)C(OCC)=O

Diethyl(phenylacetyl)malonate Usage And Synthesis

Chemical Properties

Diethyl phenylacetylmalonate contains two ester bonds, which are relatively unreactive, but which can be hydrolyzed in the presence of a suitable catalyst to produce compounds such as phenylacetic acid and ethanol. The compound can also be esterified with other alcohols to produce different ester compounds, e.g., with methanol to give methyl phenylacetylmalonate. By acid-catalyzed hydrolysis, the compound can generate phenylacetylmalonic acid, and further addition of water can obtain phenylacetic acid and diethyl malonate.

Physical properties

Diethyl(phenylacetyl)malonate has a boiling point of 120 °C. Its density is predicted to be 1.148±0.06 g/cm3.

Uses

Organic synthesis intermediates.

Preparation

The anhydrous ethanol co-vaporized with diethyl phthalate and sodium metal is added dropwise to the mixture of diethyl malonate, carbon tetrachloride and magnesium, heated to start the reaction, and the temperature is controlled to smooth the reaction. Then add anhydrous diethyl ether, heat for 1h, add the diethyl ether solution of phenylacetyl chloride (add slowly, not to make the reaction too intense). After the reaction is completed, cool and add water, separate the oil layer, and evaporate the diethyl ether under reduced pressure to obtain diethyl(phenylacetyl)malonate.

storage

Dry and cool place and keep away from strong light.