Synthesis of tetraethyl 1,1,3,3-propanetetracarboxylate

Preparation of tetraethyl 1,1,3,3-propanetetracarboxylate

Preparation of tetraethyl 1,1,3,3-propanetetracarboxylate

Preparation of tetraethyl 1,1,3,3-propanetetracarboxylate

32 g of ethyl malonate and 8 g of 40% formalin are placed in a flask, cooled by immersion in ice, and 0.5 g of diethylamine added. The flask is then cooled and left to stand for 12 hours at room temperature, after which it is heated on a boiling water bath for 5-6 hours. The aqueous layer is separated, and the residue distilled under reduced pressure (about 12 mmHg). The distillation is conducted slowly, so that all the water passes over below 50° C. Tetraethyl 1,1,3,3-propanetetracarboxylate passes over at 190-200° C. The yield of tetraethyl 1,1,3,3-propanetetracarboxylate 80% theoretical as colourless oil, insoluble in water; b.p. 198° C/12 mmHg.

Systematic organic chemistry, by W. M. Cumming, 144, 1937.

IUPAC Name

tetramethyl 2-(2-methylpropyl)propane-1,1,3,3-tetracarboxylate

InChI

InChI=1S/C15H24O8/c1-8(2)7-9(10(12(16)20-3)13(17)21-4)11(14(18)22-5)15(19)23-6/h8-11H,7H2,1-6H3

InChI Key

ISKYJZZYFSFGOC-UHFFFAOYSA-N

Canonical SMILES

CC(C)CC(C(C(=O)OC)C(=O)OC)C(C(=O)OC)C(=O)OC

Depositor-Supplied Synonyms

tetramethyl 2-(2-methylpropyl)propane-1,1,3,3-tetracarboxylate, 5457-02-3, NSC21386, AC1L5G8I, AC1Q5YQ8, CTK5A1708, AR-1L6494, NSC-21386, 2,2,4,4-Pentanetetracarboxylicacid, 3-(2-methylpropyl)-, 1,2,4,4-tetramethyl ester

Removed Synonyms

CID228449, 103-04-8

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