Synthesis of diethyl malonate (malonic acid diethyl ester)

Preparation of diethyl malonate

Preparation of diethyl malonate

Preparation of diethyl malonate

200 g of monochloroacetic acid are mixed with 50 ml of water and neutralized by the addition of 300 g of crystallized sodium carbonate. The solution is heated to 80° C and poured, with rapid stirring, into a solution of 125 g of sodium cyanide in 250 ml of water, heated to 90-95° C, and the mixture is boiled for several minutes. The reaction mixture is then cooled to room temperature and neutralized with sulfuric acid. The separated residue is filtered, and the filtrate evaporated to dryness in vacuo at 60° C. Then the residue is washed with 200 g of 94 % alcohol, filtered, the filtrate added to the residue obtained from the evaporation, warmed and again filtered. The solid is washed with a further similar quantity of alcohol, and the two alcoholic filtrates are combined and evaporated under reduced pressure. The dry residue is mixed with 600 g of absolute alcohol, 19 ml sulfuric acid (d=1.84) added, the mixture cooled to below 0° C, and saturated with dry hydrogen chloride gas. After standing for 2 hours the solution is boiled for 2 hours, then cooled and filtered. The solid is washed with 100 ml of absolute alcohol, which is then mixed with the previous filtrate. The mixture is boiled, and the vapour of 700 g of absolute alcohol passed through it, in 3-4 hours. Part of the alcohol is then distilled off, and the residue, after cooling, poured on to ice. The diethyl malonate is extracted with ether, washed with sodium carbonate, dried with calcium chloride, and distilled in vacuo, after removal of the solvent. A yield of diethyl malonate is 85-88 % with boiling point 198° C.

Organic medical chemicals, by M. Barrowliff, 40-41, 1921

IUPAC Name

diethyl propanedioate

InChI

InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3

InChI Key

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)CC(=O)OCC

MeSH Synonyms

diethyl malonate, diethylmalonate, malonic acid, diethyl ester, propanedioic acid, diethyl ester

Depositor-Supplied Synonyms

DIETHYL MALONATE, Diethyl propanedioate, 105-53-3, Malonic ester, Propanedioic acid, diethyl ester, Malonic acid, diethyl ester, Dicarbethoxymethane, Malonic acid diethyl ester, Carbethoxyacetic ester, Ethyl propanedioate, Methanedicarboxylic acid, diethyl ester, Ethyl malonate (VAN), NSC 8864, Ethyl methanedicarboxylate, 1,3-diethyl propanedioate, Propanedioic acid, 1,3-diethyl ester, diethyl propane-1,3-dioate, FEMA No. 2375, UNII-53A58PA183, IYXGSMUGOJNHAZ-UHFFFAOYSA-N, EINECS 203-305-9, AI3-00656, DSSTox_CID_1863, DSSTox_RID_76370, DSSTox_GSID_21863, CAS-105-53-3, PubChem23745, ACMC-1BUZQ, malonic acid diethylester, malonic acid-diethylester, AC1L1PHO, AC1Q34NR, AC1Q64ZO, SCHEMBL8636, WLN: 2OV1VO2, D97754_ALDRICH, KSC176I2R, W237507_ALDRICH, propanedioic acid diethyl ester, CCRIS 9480, CHEMBL177114, CTK0H6428, NSC8864, MolPort-000-871-970, BB_SC-7073, NSC-8864, STR00319, Tox21_201362, Tox21_302931, ANW-15239, AR-1J3789, BBL027742, SBB040813, STL281878, ZINC01648281, AKOS000118957, 53A58PA183, LS-2662, MCULE-8243470790, RP22330, NCGC00249033-01, NCGC00256502-01, NCGC00258914-01, AJ-28737, AK120896, AN-24716, BC226841, CJ-26651, I803, TC-103984, FT-0083188, FT-0624843, M0029, ST24046561, ST50214386, 14074-EP2270009A1, 14074-EP2275395A2, 14074-EP2284148A1, 14074-EP2284159A1, 14074-EP2292595A1, 14074-EP2298768A1, 14074-EP2308839A1, 14074-EP2308867A2, 14074-EP2308870A2, 14074-EP2316836A1, 3B3-024340, 3B3-027076, 3B3-046694, PROPANEDIOIC ACID,DIETHYL ESTER (MALONIC ACID,DIETHYL ESTER), InChI=1/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H

Removed Synonyms

Ethyl malonate, DiethylMalonate, CID7761, C498810, 1060-33-9, 145601-68-9

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