Synthesis of diethyl 2,3-diacetylbutanedioate

Preparation of diethyl 2,3-diacetylbutanedioate

Alternative Names: Diethyl 2,3-diacetylsuccinate; Diethyl 2,3-diacetylbutanedioate; Butanedioic acid, 2,3-diacetyl-, diethyl ester;

Preparation of diethyl 2,3-diacetylbutanedioate

Preparation of diethyl 2,3-diacetylbutanedioate

In a stoppered bottle of 500 ml capacity provided with a reflux condenser 25 g acetoacetic ester are dissolved in 150 g pure ether which has been dried over sodium, and to this solution 5 g sodium are added, preferably in the form of fine wire. The wire is made with the aid of a press. During the pressing it is necessary to let the wire fall straight into ether, or, better, into toluene, in order to protect it from the moisture of the air. A vigorous evolution of hydrogen accompanies the gradual conversion of the sodium into an extremely finely divided mass of sodium-acetoacetic ester. The main reaction is complete in 1-2 hours. Part of the sodium is then so covered by the sodium-acetoacetic ester that it is not further acted upon. The bottle is therefore closed for a moment with the stopper and vigorously shaken. The metal becomes bright again, and the evolution of hydrogen begins afresh. If this operation is repeated a few times, the metal disappears in a comparatively short time. 20 g finely powdered iodine are now dissolved in pure ether, and the solution added in small portions, with constant shaking, to the sodium-acetoacetic ester. The reaction takes place at once, and a large amount of sodium iodide is precipitated. As soon as the color of the iodine no longer vanishes at once the solution is filtered, the ether evaporated off, and the diethyl 2,3-diacetylbutanedioate allowed to solidify. It is then pressed on a porous tile, and recrystallized from warm 50 % acetic acid.

Introduction to the preparation of organic compounds, E. Fisher, 73-74, 1909

IUPAC Name

diethyl 2,3-diacetylbutanedioate

InChI

InChI=1S/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

InChI Key

GJEDSIHWCPPJFN-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)C(C(C(=O)C)C(=O)OCC)C(=O)C

MeSH Synonyms

3,4-DCHDO, 3,4-dicarbethoxyhexane-2,5-dione

Depositor-Supplied Synonyms

Diethyl 2,3-diacetylsuccinate, 2049-86-7, 2ovyv1&v1&vo2, diethyl 2,3-diacetylbutanedioate, Butanedioic acid, 2,3-diacetyl-, diethyl ester, GJEDSIHWCPPJFN-UHFFFAOYSA-N, Diethyl 2,5-dioxohexane-3,4-dicarboxylate, 2,3-diacetyl-Butanedioicacid 1,4-diethylester, Butanedioic acid, 2,3-diacetyl-, 1,4-diethyl ester, 141862-02-4, Diethyl diacetylsuccinate, AC1Q5C1C, diethyl2,3-diacetylsuccinate, AC1L3U89, SCHEMBL4944171, CTK8E5776, NSC6782, MolPort-001-781-425, 3,4-Dicarbethoxyhexane-2,5-dione, NSC 6782, NSC-6782, EINECS 218-073-4, AR-1E4543, CL 946, STK523657, AKOS005454531, MCULE-1931739490, diethyl 2,3-diacetylbutane-1,4-dioate, OR060625, OR240312, ST001744, AI3-06163, DB-066222, TR-009563, Butanedioic acid,3-diacetyl-, diethyl ester, FT-0675952, 1,4-DIETHYL 2,3-DIACETYLBUTANEDIOATE, A18422, 3,4-BIS(ETHOXYCARBONYL)HEXANE-2,5-DIONE, BUTANEDIOIC ACID 2,3-DIACETYL-,DIETHYL ESTER, A2428/0102824

Removed Synonyms

CID95399, 20926-64-1

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