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
A major drawback of malonic ester synthesis is that the alkylation stage can also produce dialkylated structures. This makes separation of products difficult and yields lower.[3]
^Cite error: The named reference heat condition was invoked but never defined (see the help page).
^House, Herbert O. (1972). Modern Synthetic Reactions. Menlo Park, CA.: W. A. Benjamin. ISBN 0-8053-4501-9.
^Malonic Ester Synthesis – Alkylation of Enolates
and 28 Related for: Malonic ester synthesis information
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...
specifically an α-substituted acetone. This is very similar to malonicestersynthesis. A strong base deprotonates the dicarbonyl α-carbon. This carbon...
malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from...
of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester...
acetonedicarboxylic acid ester and a diacyl (1,2 ketone). The mechanism operates in the same way as the Knoevenagel condensation: Malonicestersynthesis Aldol condensation...
condensation. This conversion is exploited in the malonicestersynthesis, wherein the diester of malonic acid reacts with an electrophile (e.g., alkyl halide)...
NaCl + CF2 + CO2 Decarboxylations are an important in the malonic and acetoacetic estersynthesis. The Knoevenagel condensation and they allow keto acids...
acetamidomalonate (DEAM) is a derivative of malonic acid diethyl ester. Formally, it is derived through the acetylation of ester from the unstable aminomalonic acid...
which are often used in organic synthesis. Examples include the Knoevenagel condensation and the malonicestersynthesis. Examples of compounds which contain...
an aromatic malonicester used in the synthesis of moderate to long lasting barbiturates such as phenobarbital. Unlike other malonicesters that are derived...
acetoacetate is often used in the acetoacetic estersynthesis similar to diethyl malonate in the malonicestersynthesis or the Knoevenagel condensation. A subsequent...
cytosolic fatty acid synthesis, there is also mitochondrial fatty acid synthesis (mtFASII), in which malonyl-CoA is formed from malonic acid with the help...
condensation and malonicestersynthesis. Sodium ethoxide may either deprotonate the α-position of an ester molecule, forming an enolate, or the ester molecule...
Knoevenagel condensation and the first steps of the malonicestersynthesis and acetoacetic estersynthesis). Otherwise, the most acidic carbonyls are typically...
transesterification reactions that yield ethyl esters. Sodium or potassium ethoxide is also a suitable base for the malonicestersynthesis where diethyl malonate is used...
Conversion of this compound with malonic acid to (−)-strychnine 11 was already known as a procedure. The 1993 Keuhne synthesis concerns racemic strychnine...
rats) is 1.5 g/kg. Harald Strittmatter, Stefan Hildbrand and Peter Pollak Malonic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry...
quinolol. The compound is then condensed with ethoxy methylene malonic diethyl ester (EMME) and cyclized thermally (2). That intermediate is then saponified;...
laboratory synthesis of a pyrimidine was not carried out until 1879, when Grimaux reported the preparation of barbituric acid from urea and malonic acid in...
traditional Hurtley reaction, the carbon nucleophiles were derived from malonicester and other dicarbonyl compounds: Z2CH2 + BrC6H4CO2H + KOH → Z2C(H)−C6H4CO2H...
carboxylate ester and a nitrile. It is a colourless liquid with a pleasant odor. This material is useful as a starting material for synthesis due to its...
Säuren" [On the addition of sodium acetoacetate- and sodium malonic acid esters to the esters of unsaturated acids]. Journal für Praktische Chemie. 2nd...
from malonic acid, urea, and phosphorus oxychloride (POCl3). Malonic acid has since been replaced by diethyl malonate, because using the ester avoids...
particular by the reaction of malonicester derivatives with derivatives of urea. The resulting allyl-(1-methyl-2-pentynyl) malonicester is synthesized by subsequent...
reagents to form ketones. A C-C acylation reaction can occur with a malonicester-type compound, in the following scheme useful for syntheses of macrolide...
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