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Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B 1, and vitamin B 6.
The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha (directly adjacent) to both carbonyl groups, and then converted to a substituted acetic acid. [2] Reaction formula
Chemical structure of the malonate dianion. Malonic acid is diprotic; that is, it can donate two protons per molecule. Its first is 2.8 and the second is 5.7. [2] Thus the malonate ion can be HOOCCH 2 COO − or CH 2 (COO) 2− 2. Malonate or propanedioate compounds include salts and esters of malonic acid, such as Diethyl malonate
Barbital was prepared by condensing diethylmalonic ester with urea in the presence of sodium ethoxide, or by adding at least two molar equivalents of ethyl iodide to the silver salt of malonylurea (barbituric acid) or possibly to a basic solution of the acid. The result was an odorless, slightly bitter, white crystalline powder.
Classical examples of the Michael reaction are the reaction between diethyl malonate (Michael donor) and diethyl fumarate (Michael acceptor), [26] that of diethyl malonate and mesityl oxide (forming Dimedone), [27] that of diethyl malonate and methyl crotonate, [28] that of 2-nitropropane and methyl acrylate, [29] that of ethyl ...
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Diethyl diethylmalonate or diethyl 2,2-diethylmalonate is a derivative of diethyl malonate. It can be used in the synthesis of barbital. [2] Uses