Diethyl benzylmalonate

In an analogous way, by the action of the equivalent amount (exactly 1 mole) of benzyl chloride on diethyl sodiomalonate, diethyl benzylmalonate, and finally hydrocinnamic acid, are formed. 

In a previously flame-dried 1-1. three-necked, round-bottomed flask equipped with a mechanical stirrer, dropping tube, and reflux condenser fitted with a calcium chloride tube are placed 20.5 g. (0.5 mole) of a 58.5 X, dispersion of sodium hydride in mineral oil (Metal Chemicals Division, Ventron Corporation) and 200 ml. of dimethyl sulfoxide. The mixture is stirred at 20- 25, with occasional ice-bath cooling, and a solution of 123.1 g. (0.5 mole) of diethyl benzylmalonate (Aldrich) is added dropwise. Stirring is continued at 20-25" for about 30 min. (until the evolution of hydrogen is complete), then a solution of 53.8 g. (0.5 mole) of 2-dimethylaminocthyl chloride is added dropwise. After the addition is completed the stirred mixture is gradually heated to 100°. After 30 min. the mixture is cooled and poured into I 1. of ice water. The mixture is extracted with three l50-ml. portions of ether and the combined ethereal solution is dried over magnesium sulfate and transferred to a 1-1. three-necked, round-bottomed flask equipped with a mechanical stirrer, dropping funnel, and air condenser, and then... 

When Mn(OAc)rmediated electrochemical oxidation of diethyl benzylmalonate is conducted in the presence of an alkyne or alkene, hydronaphthalene derivatives appear as products. ... 

Method One, Marvel s (556) modification of Fischer s (283) procedure. Diethyl benzylmalonate is prepared in 55% yield from sodium, absolute see p. 360 see p. 861. 

PreparaMon of Aldehydes and Ketones. Monosubstituted malonyl azides can be synthesized readily from the dihydrazides. Urethans of /em-diamines result when the azides are rearranged in alcohol these urethans are hydrolyzed rapidly by mineral adds to aldehydes. Diethyl benzylmalonate can be converted to phenylacetaldehyde in about 70% yield by this procedure. ... 

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