Synthesis of acetoacetic ester (ethyl acetoacetate)

Preparation of acetoacetic ester

500 ml round bottom flask connected with a reflux condenser is charged with 200 g of carefully dried ethyl acetate. The flask is cooled with cold water and 20 g of sodium in thin sliced or wire are added. After a short time a brisk reaction sets in and ultimately the liquid starts to boil. When the action slackens the flask is heated until the sodium completely dissolved. With proper stirring about 100 ml of 50% acetic acid solution is at once added until the liquid is acid and then an equal volume of concentrated brine. The liquid divides into two layers the upper one, consisting of acetoacetic ester and unchanged ethyl acetate, is carefully separated and distilled collecting fraction passing at 100° C. The distillate is redistilled and collected in fractions, that distilling at 175-185° C is nearly pure acetoacetic ester. Yield 30-40 g. A better yield is obtained if the fractionation is conducted under reduced pressure.

A Class-Book of Organic Chemistry, by J. B. Cohen, 15, 1919

IUPAC Name

ethyl 3-oxobutanoate

InChI

InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

InChI Key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)CC(=O)C

MeSH Synonyms

ethyl 3-oxobutanoate, ethyl acetoacetate, ethyl acetoacetate, 1,2-(14)C-labeled, ethyl acetoacetate, 1,3-(14)C-labeled, ethyl acetoacetate, 14C4-labeled, ethyl acetoacetate, 2,4-(14)C-labeled, ethyl acetoacetate, 2-(14)C-labeled, ethyl acetoacetate, 3-(14)C-labeled

Depositor-Supplied Synonyms

ethyl acetoacetate, ethyl 3-oxobutanoate, ethyl acetylacetate, ethyl 3-oxobutyrate, diacetic ether, 141-97-9, Acetoacetic ester, 3-oxobutanoic acid ethyl ester, acetoacetic acid, ethyl ester, ethyl acetylacetonate, 3-Oxo-butyric acid ethyl ester, Butanoic acid, 3-oxo-, ethyl ester, Active acetylacetate, active acetyl acetate, ethyl beta-ketobutyrate, Ethyl acetyl acetate, Ethylacetacetat, 3-Oxobutyric Acid Ethyl Ester, ethyl-acetoacetate, 1-Ethoxybutane-1,3-dione, ACETOACETIC ACID ETHYL ESTER, Acetoctan ethylnaty, Ethylacetacetat [Czech], NSC 8657, Acetoacetic acid ethylester, UNII-IZP61H3TB1, Acetoctan ethylnaty [Czech], Ethylester kyseliny acetoctove, FEMA No. 2415, CCRIS 1343, CHEBI:4893, HSDB 402, EAA, butanoic acid, 3-oxo-ethyl ester, XYIBRDXRRQCHLP-UHFFFAOYSA-N, EINECS 205-516-1, Ethylester kyseliny acetoctove [Czech], AI3-00066, ethyl acetoacetat, Ethyl actoacetate, EAC, Ethyl-3-oxobutyrate, ethyl-3-oxobutanoate, ethyl 3-oxo-butyrate, ethyl 3-oxo-butanoate, ethyl-3-oxo-butanoate, acetoacetate ethyl ester, ethyl alpha-acetoacetate, ACMC-209cnd, AC1L1RUV, ethyl 3-keto-n-butanoate, DSSTox_CID_7092, bmse000944, AC1Q1K3Y, AC1Q34NY, DSSTox_RID_78305, IZP61H3TB1, DSSTox_GSID_27092, SCHEMBL15500, ethyl 3-oxidanylidenebutanoate, KSC176S2B, 10912_ALDRICH, W241504_ALDRICH, W241512_ALDRICH, WLN: 2OV1V1, 3-ketobutyric acid ethyl ester, 537349_ALDRICH, CHEMBL169176, Jsp002472, 3-oxo-butanoic acid ethyl ester, 00410_FLUKA, 00420_FLUKA, 10912_FLUKA, CTK0H6920, NSC8657, MolPort-000-872-028, BB_SC-7092, NSC-8657, Tox21_200645, AC-671, AN-909, ANW-20663, AR-1H6421, BBL012204, SBB040867, STL163546, ZINC05650471, AKOS000118955, LS-2378, MCULE-8615117086, RP17313, RTR-032364, NCGC00248778-01, NCGC00258199-01, AK163244, BC202411, CAS-141-97-9, KB-77205, TR-032364, A0649, FT-0621773, ST50214457, C03500, 13021-EP2275395A2, 13021-EP2280012A2, 13021-EP2287165A2, 13021-EP2287166A2, 13021-EP2292615A1, 13021-EP2292620A2, 13021-EP2295438A1, 13021-EP2299785A1, 13021-EP2305825A1, 13021-EP2306788A1, 13021-EP2306789A1, 13021-EP2308838A1, 13021-EP2316831A1, 19134-EP2305668A1, 19134-EP2314576A1, 3B4-0867, S14-1425, InChI=1/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H

Removed Synonyms

Ethyl acetoacetate sodium salt, CID8868, 115271-29-9, 1435-12-7, 4433-85-6, ACE

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