Synthesis of diethyl diethylmalonate

Preparation of diethyl diethylmalonate

Preparation of diethyl diethylmalonate

Preparation of diethyl diethylmalonate

All reagents and reaction set-up must be completely dry. For the synthesis 100 g of carefully dried and freshly distilled malonic acid ethyl ester, 28.8 g of sodium, 380 ml of absolute alcohol, and 195 g of carefully dried and freshly distilled ethyl iodide are required. 14.4 g of the sodium is dissolved in 190 ml of the alcohol under a reflux condenser protected by a calcium chloride tube, the malonic ester added with stirring, and then slowly through a dropping funnel 97.5 g of the ethyl iodide. The mixture is finally boiled, and when the pH become neutral the second half of the sodium (14.4 g) is dissolved in the rest of the alcohol (190 ml), and the equivalent amount of the ethyl iodide (97.5 g) slowly added, after which the mixture is boiled over night. Alcohol is removed by evaporation, and residue is treated with ether and water. The two layers are separated, and the ethereal solution is dried over the sodium sulfate. Ether is removed in vacuum and final product is distilled yielding 112 g or 83 % of diethyl diethylmalonate boiling at 220-222° C. Redistillation gives 102.5 g boiling at 221-222° C.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 64-65, 1923

IUPAC Name

diethyl 2,2-diethylpropanedioate

InChI

InChI=1S/C11H20O4/c1-5-11(6-2,9(12)14-7-3)10(13)15-8-4/h5-8H2,1-4H3

InChI Key

ZKBBUZRGPULIRN-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

Diethyl diethylmalonate, 77-25-8, Diethylmalonic ester, Diethyl 2,2-diethylmalonate, Diethylmalonate diethyl ester, Diethylmalonic acid diethyl ester, Propanedioic acid, diethyl-, diethyl ester, Diethylmalonic acid, diethyl ester, ZKBBUZRGPULIRN-UHFFFAOYSA-N, 1,3-diethyl 2,2-diethylpropanedioate, Propanedioic acid, 2,2-diethyl-, 1,3-diethyl ester, diethyl 2,2-diethylpropanedioate, Diethyldiethylmalonate, ACMC-209p8s, DIethyl-DIETHYLMALONATE, AC1L24RQ, UNII-CEH13944YQ, KSC644C0H, Diethyl Diethylmalonate Diethyl, 156817_ALDRICH, AC1Q322K, CEH13944YQ, Diethyl 2,2-diethylmalonate #, SCHEMBL1244565, CTK5E4103, Diethyl 3,3-pentanedicarboxylate, NSC8710, diethyl-malonic acid diethyl ester, MolPort-001-783-062, NSC 8710, NSC-8710, EINECS 201-016-2, ANW-36986, ZINC01648195, AKOS009157408, Malonic acid, diethyl-, diethyl ester, MCULE-9331370148, AJ-28719, AK117211, CJ-05920, CJ-26610, KB-76557, M284, 2,2-diethyl-propanedioic acid diethyl ester, AI3-05640, DB-056197, RT-001736, D0867, FT-0624835, ST24030334, ST50825662, Malonic acid, diethyl-, diethyl ester (8CI), I14-7535, Propanedioic acid,2,2-diethyl-, 1,3-diethyl ester, 3B3-027216, 3,3-PENTANEDICARBOXYLIC ACID,DIETHYL ESTER (DIETHYL MALONATE,DIETHYL ESTER), InChI=1/C11H20O4/c1-5-11(6-2,9(12)14-7-3)10(13)15-8-4/h5-8H2,1-4H

Removed Synonyms

Malonic acid, diethyl ester, Propanedioic acid, diethyl ester, CID66165

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