Dimethyl malonate is a

diester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are ...

derivative of

malonic acid Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ...

. It is a common reagent for

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

used, for example, as a precursor for

barbituric acid Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid ...

. It is also used in the

malonic ester synthesis 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. The major dr ...

. It can be synthesized from

dimethoxymethane Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimetho ...

and

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

. ::

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Dimethyl malonate is used extensively in the fragrance industry as a raw material in the synthesis of jasmonates. For example, methyl dihydrojasmonate is synthesized from

cyclopentanone Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid. Preparation Upon treatment with barium hydroxide at elevated temperatures, adipic acid undergoes ketonization to give cyclopenta ...

pentanal Pentanal (also called valeraldehyde) is the organic compound is an alkyl aldehyde, molecular formula C5H10O. It is used in flavorings, resin chemistry, and rubber accelerators. Its smell is described as fermented, bready, fruity, nutty, berry. ...

and dimethyl malonate. Hedione is used in almost all fine fragrances and is found in Christian Dior's ''Eau Sauvage'' and "Diorella", Hermes' "Voyage d'Hermes Parfum", Calvin Klein's "CKOne", Chanel's "Chanel No. 19", and Mark Jacob's "Blush", among others. As of 2009, Hedione was Firmenich's top selling compound by volume. Hebei Chengxin is the world's largest producer of dimethyl malonate by volume and uses a chloroacetic acid/sodium cyanide process developed in the 1940s.Stoesser, WC. "Preparation of malonic esters,
US Patent 2337858
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References

{{Reflist Methyl esters Malonate esters Reagents for organic chemistry

See also

References