Synthesis of diethyl ethylmalonate

Preparation of diethyl ethylmalonate

Preparation of diethyl ethylmalonate

Preparation of diethyl ethylmalonate

2.3 g of sodium are dissolved in 25 g of absolute alcohol in a small flask connected with a reflux condenser and a dropping funnel. The yielded sodium ethoxide solution is gradually treated with 16 g of cooled diethyl malonate. The transparent crystals of sodium ethoxide separating out at first pass over into a voluminous pasty mass of sodium malonic ester. This mass is treated from the dropping funnel with 20 g of ethyl iodide (or equal amount of ethyl bromide) in small portions with shaking. The reaction mixture is then heated until the liquid no longer shows an alkaline reaction, for which one or two hours may be necessary. The alcohol is removed by evaporation, the residue is treated with water and reaction product is extracted with ether.  The ether is evaporated, and the residue distilled collecting fraction passing at 206-208° C. The yield of diethyl ethylmalonate is about 15 g.

The practical methods of organic chemistry, by L. Gattermann, 162, 1909

IUPAC Name

diethyl 2-ethylpropanedioate

InChI

InChI=1S/C9H16O4/c1-4-7(8(10)12-5-2)9(11)13-6-3/h7H,4-6H2,1-3H3

InChI Key

VQAZCUCWHIIFGE-UHFFFAOYSA-N

Canonical SMILES

CCC(C(=O)OCC)C(=O)OCC

Depositor-Supplied Synonyms

DIETHYL ETHYLMALONATE, 133-13-1, Diethyl 2-ethylmalonate, Propanedioic acid, ethyl-, diethyl ester, diethyl 2-ethylpropanedioate, Ethylmalonic acid diethyl ester, VQAZCUCWHIIFGE-UHFFFAOYSA-N, Malonic acid, ethyl-, diethyl ester, SBB060956, Propanedioic acid, 2-ethyl-, 1,3-diethyl ester, diethyl 2-ethylpropane-1,3-dioate, diethyl ethyl-malonate, ACMC-209brf, AC1L1RCG, Diethyl ethylpropanedioate, AC1Q63TJ, UNII-69G92OYR3M, D95204_ALDRICH, KSC492S9F, SCHEMBL230068, 69G92OYR3M, CTK3J2992, NSC8706, 1,3-diethyl 2-ethylpropanedioate, MolPort-000-219-476, 2-ethyl-malonic acid diethyl ester, NSC 8706, NSC-8706, EINECS 205-093-3, ANW-19513, AR-1I4693, ZINC01648192, 2-ethylpropanedioic acid diethyl ester, AKOS002710245, MCULE-9474149783, RP17466, AK167609, AN-43709, CJ-26607, SC-26633, AI3-19481, RT-001185, E0138, FT-0624783, Malonic acid, ethyl-, diethyl ester (8CI), ST51047044, A806565, 3B4-0687, I14-6119, 1,1-PROPANEDICARBOXYLIC ACID,DIETHYL ESTER (MALONIC ACID,ETHYL,DIETHYL ESTER), InChI=1/C9H16O4/c1-4-7(8(10)12-5-2)9(11)13-6-3/h7H,4-6H2,1-3H, 581796-72-7

Removed Synonyms

Ethyl diethylmalonate, Malonic acid, diethyl ester, Propanedioic acid, diethyl ester, CID8610, 93264-17-6, 99-19-4

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