Synthesis of diethyl tartrate

Preparation of diethyl tartrate

Preparation of diethyl tartrate

Preparation of diethyl tartrate

Finely powdered tartaric acid is shaken with rather more than its own weight of absolute alcohol, and then saturated with dry hydrochloric acid gas, the whole being well cooled with ice. The mixture is allowed to stand for at least twenty-four hours, and then the supernatant liquid poured off from the unchanged acid. The greater part of the hydrochloric acid is removed from the solution by blowing air through it. The excess of alcohol and water is then removed by distilling in vacuo from the water-bath. The residue consists chiefly of the acid ester. It is taken up with the same amount of absolute alcohol as was used previously, and the well-cooled solution again saturated with hydrochloric acid. After standing, it is treated exactly as before, and the residue, which does not distil from the water-bath, then fractionated in vacuo. After refractionation the ester forms a colourless viscous liquid which boils at 155° C at 11 mm. and 162° C at 19 mm. It solidifies on standing to a mass of colourless crystals which melt at 48° C.

Preparation of organic compounds, E. de. Barry Barnett, 177-178, 1912

IUPAC Name

diethyl 2,3-dihydroxybutanedioate

InChI

InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3

InChI Key

YSAVZVORKRDODB-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

diethyl tartrate, diethyl tartrate, (S-(R*,R*))-isomer, tartaric acid diethyl ester

Depositor-Supplied Synonyms

Diethyl tartrate, Ethyl tartrate, Diethyl L-tartrate, Diethyl (+)-tartrate, (+)-Diethyl L-tartrate, Tartaric acid, diethyl ester, Ethyl (+)-tartrate, L-(+)-(Diethyl tartrate), (+)-Tartaric acid diethyl ester, [-]-Tartaric acid diethyl ester, Diethyl 2,3-dihydroxybutanedioate, YSAVZVORKRDODB-UHFFFAOYSA-N, Butanedioic acid, 2,3-dihydroxy-, diethyl ester, Diethyl (2R,3R)-(+)-tartrate, DIETHYL-D-TARTRATE, racemic-Dimethoxysuccinic acid, dimethyl ester, Tartaric acid, (R,R)-, Diethyl (2R,3R)-tartrate, Diethyl (R,R)(+)tartrate, Ethyl tartarate, Diethyl 1,2-ethanedicarboxylate, (-)-Tartaric acid diethyl ester, Butanedioic acid, 2,3-dihydroxy- [R-(R*,R*)]-, diethyl ester, Butanedioic acid,3-dihydroxy-, diethyl ester, L-(+)-Diethyl l-Tartrate, Diethyl 2,3-dihydroxysuccinate, (-)-DIETHYL-D-TARTRATE, Butanedioic acid,3-dihydroxy- [R-(R*,R*)]-, diethyl ester, Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-diethyl ester, diethyl tartarate, (+)-diethyltartrate, L -DiethylL-tartrate, (+)-diethyl tartrate, (-)-diethyl tartrate, ACMC-209cfd, ACMC-209qql, AC1L1WWT, Tartaric acid diethyl ester, SCHEMBL112148, AC1Q325U, CTK1D4249, NSC8878, MolPort-006-110-372, NSC-8878, NSC44808, NSC-44808, AKOS009031375, 1,4-diethyl 2,3-dihydroxybutanedioate, AN-1442, MCULE-4370893161, TRA0075548, TRA0088447, CA010585, CA012228, LP050505, OR004357, OR268186, Racem-dimethoxysuccinic acid, dimethylester, ST51051450, M-2159, 67926-EP2289887A2, 67926-EP2289888A2, 67926-EP2308874A1, I14-0046, I14-6997, 3B3-003667, Butanedioic acid, 2,3-dihydroxy-, diethyl ester, [S-(R*,R*)]-, Butanedioic acid, 2,3-dihydroxy-, diethyl ester, (R*,R*)-(.+/-.)-, 408332-88-7, 57968-71-5

Removed Synonyms

(-)-Diethyl D-tartrate, Diethyl L-(+)-Tartrate, L(+)-Diethyl L-tartrate, Diethyl D-(-)-Tartrate, (+)-DIETHYL-L-TARTRATE, CID62333, D-(-)-Tartaric acid diethyl ester, L-(+)-Tartaric acid diethyl ester, 87-91-2, NSC 44808, Tartaric acid, diethyl ester, (R,R)-, 13811-71-7, Diethyl 1,2-dihydroxy-1,2-ethanedicarboxylate, Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, diethyl ester

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