2049-86-7

Usage

Uses

Used in Food and Beverage Industry:
Diethyl 2,3-diacetylsuccinate is used as a flavoring additive for its fruity, sweet aroma, enhancing the taste and aroma of various food and beverage products. It is particularly popular in the production of baked goods, confectionery, and beverages, where it imparts a pleasant and appealing flavor profile.
Used in Perfume and Fragrance Industry:
Diethyl 2,3-diacetylsuccinate is used as a fragrance ingredient in the perfume and fragrance industry. Its sweet and fruity scent contributes to the creation of various scent profiles, adding depth and complexity to perfumes, colognes, and other fragranced products.

InChI:InChI=1/C12H18O6/c1-5-17-11(15)9(7(3)13)10(8(4)14)12(16)18-6-2/h9-10H,5-6H2,1-4H3

Upstream product

• 2439-85-2 N-bromophthalimide 
• 141-97-9 ethyl acetoacetate 
• 854413-19-7 4-acetyl-2-methyl-5-oxo-4,5-dihydro-furan-3-carboxylic acid ethyl ester 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 625-01-4 ethyl chlorosulfate 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 1114-30-3 diethyl 2,3-dibromosuccinate 
• 1114-31-4 diethyl meso-2,3-dibromosuccinate 
• 75-07-0 acetaldehyde 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 7732-18-5 water 
• 99-98-9 N,N-dimethyl-p-phenylenediamine radical cation 
• 128-08-5 N-Bromosuccinimide 

Downstream Products

• 58412-50-3 1-benzoylamino-2,5-dimethyl-pyrrole-3,4-dicarboxylic acid diethyl ester 
• 94263-56-6 2,5-dimethyl-1-(4-sulfamoyl-phenyl)-pyrrole-3,4-dicarboxylic acid diethyl ester 
• 131970-78-0 2,5,2',5'-tetramethyl-1,1'-ethanediyl-bis-pyrrole-3,4-dicarboxylic acid tetraethyl ester 
• 52175-96-9 2,5-dimethyl-1-phenyl-pyrrole-3,4-dicarboxylic acid 
• 594864-22-9 diethyl 2,5-dimethyl-1-phenyl-1H-pyrrole-3,4-dicarboxylate 
• 83607-08-3 1,4-bis-(3,4-bis-ethoxycarbonyl-2,5-dimethyl-pyrrol-1-yl)-benzene 
• 58412-55-8 2,5-dimethyl-1-(2-phenyl-acetylamino)-pyrrole-3,4-dicarboxylic acid diethyl ester 
• 64-17-5 ethanol 
• 144-62-7 oxalic acid 
• 64-19-7 acetic acid 
• 1723-25-7 ethyl 2,3-dioxobutyrate 

Relevant academic research and scientific papers

Transition metal salts mediated oxidative radical addition of ethyl acetoacetate to limonene

Transition metal salts mediated oxidative radical addition of ethyl acetoacetate to limonene produced chemo-and regiospecificaly (1'R,5RS)-3-carboethoxy-2,5-dimethyl-5-(4'-methylcyclohexen-3'-enyl)-4,5- dihydrofuran as a 1:1 mixture of diastereoisomers. The best yield (72 % isolated) was obtained using limonene (1 mol equiv.), ethyl acetoacetate (1 mol equiv.) and Mn(OAc)3?2H2O (2 mol equiv.) in acetic acid at 70°C. The utilisation of cerium(IV) ammonium nitrate (CAN) or Co(OAc)2 instead of Mn(III) led to lower yields of the dihydrofurans along with diethyl 2,3-diacetylsuccinate. Fe(III) salts gave a complex mixture of products and using CuCl2 there was no reaction.

Reaction of N-chloroamines with carbanions derived from ethyl acetoacetate and diethyl malonate

Carbanions derived from ethyl 3-oxobutanoate and diethyl malonate reacted with an equimolar amount of N-chloro-N-ethylethanamine, N-chloromorpholine, or N-chloropiperidine to give diethyl 2,3-diacetylbutanedioate and tetraethyl ethane-1,1,2,2-tetracarboxylate in 68–83% yield. The possibility of heterocoupling of ethyl 3-oxobutanoate and diethyl malonate carbanions by the action of N-chloro-N-ethylethanamine and the effect of the molar reactant ratio on the selectivity of oxidative homo- and heterocoupling were studied.

Tuning the thermodynamic onset potential of electrocatalytic O2 reduction reaction by synthetic iron-porphyrin complexes

A porphyrin ligand with two β-pyrrolic electron withdrawing ester groups is synthesized and its Co complex is crystallographically characterized. The iron complex of this porphyrin ligand shows an ～200 mV positive shift in its FeIII/II potential in organic as well as aqueous solvents and in the onset potential of ORR relative to that of an unsubstituted porphyrin.

A simple preparation of ethyl 2,5-dimethylfuran-3-carboxylate and 2,5-dimethylfuran-3,4-dicarboxylic acid from diethyl 2,3-diacetylsuccinate

(Chemical Equation Presented) A simple preparation of ethyl 2,5-dimethylfuran-3-carboxylate (3), 2,5-dimethylfuran-3,4-dicarboxylic acid (4), and diethyl 2,5-dimethylfuran-3,4-dicarboxylate (5) by treatment of diethyl 2,3-diacetylsuccinate (2) with aqueous HCl is reported. The reaction is performed under organic solvent free conditions from a readily available cheap starting material.

Efficient selective formation of C-C single bonds and C=C double bonds by NBS-promoted oxidative coupling of β-keto esters

A new application of NBS, which results in the oxidative coupling of β-keto esters to selectively form C-C single and C=C double bonds, can be controlled by the amount of NBS and t-BuOK employed. This methodology adds a new entry to C-C single and C=C double-bond formation between active methylene groups under mild conditions with high selectivity. Copyright Taylor & Francis Group, LLC.

Sequential Diels - Alder reaction of in situ generated 2,3-dimethylenepyrrole and carbodienophiles: Rapid synthesis of 2,3,6,7-tetrasubstituted carbazoles

(formula presented) 2,3,6,7-Tetrasubstituted-1,2,3,4,5,6,7,8-octahydrocarbazoles 2 were synthesized in 46-90% yields by sequential Diels-Alder reactions from N-benzyl-2,5-dimethyl-3,4-bisacetoxymethylpyrrole (1) and dienophiles such as maleic anhydride, maleimides, ethyl maleate, fumaronitrile, and ethyl acrylate. The 2,3,6,7-tetrasubstituted carbazoles 3 were then synthesized in 32-87% yields from 2 by oxidation with DDQ.

Oxidative Dimerization of CH Acids

Anodic oxidation of alkyl- (1) and acylmalonic acid esters (7) yields the dehydrodimers 4 and 8, respectively.Preparative electrolyses are performed in acetonitrile in the presence of a base to generate the carbanion corresponding to the CH acid.The carbanions are oxidized to the radicals which dimerise on the electrode surface.The yields of the preparative electrolyses and the formation of the dehydrodimers 4 and 8 are discussed in terms of the CH acidity and enolization of the starting materials. - Key Words: Electrochemistry / Oxidation, anodic / CH Acids / Dehydrodimerization

ELECTROCHEMICAL OXIDATIVE DIMERIZATION OF ACETOACETIC AND BENZOYLACETIC ESTERS IN THE PRESENCE OF METAL HALIDES

Acetoacetic and benzoylacetic esters dimerize on electrolysis in the presence of metal halide mediators to form 2,5-dioxohexane-3,4-dicarboxylic and 1,4-dioxo-1,4-diphenylbutane-2,3-dicarboxylic esters in yields up to 90percent.Primarily the meso-form of the dimer is produced (up to 90percent) under optimal conditions (NaI, -20 deg C) in acetone and acetonitrile.Diastereomers of the dimer are produced in comparable amounts in methanol and ethanol.