Synthesis of ethyl iodoacetate

Preparation of ethyl iodoacetate

Ethyl iodoacetate can not be prepared directly by esterification of iodoacetic acid with ethyl alcohol but it could be prepared by reacting potassium iodide with ethyl chloroacetate or ethyl bromoacetate.

Preparation of ethyl iodoacetate

Preparation of ethyl iodoacetate

In the round bottom flask with reflux condenser 25 g of ethyl chloroacetate are dissolved in 150 ml ethyl alcohol. To alcoholic solution the solution of 35 g of potassium iodide in 25 ml distilled water is dropwise added. The mixture is stirred and gently heated at 40-50° C. After 1-2 hours the reaction is complete and the mixture is transferred to a separatory funnel with water. The oily layer is separated, dried over calcium chloride and distilled. Ethyl iodoacetate is a colorless, dense liquid boiling at 179° C. Ethyl iodoacetate is sensitive to light and should be stored in a dark place in order to prevent decomposition.

The war gases chemistry and analysis, by M. Sartory, 121-122, 1939.

IUPAC Name

ethyl 2-iodoacetate

InChI

InChI=1S/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3

InChI Key

MFFXVVHUKRKXCI-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)CI

Depositor-Supplied Synonyms

ETHYL IODOACETATE, ethyl 2-iodoacetate, Ethyl monoiodoacetate, 623-48-3, Acetic acid, iodo-, ethyl ester, Iodoacetic acid, ethyl ester, MFFXVVHUKRKXCI-UHFFFAOYSA-N, Acetic acid, 2-iodo-, ethyl ester, EINECS 210-796-3, Ethylester kyseliny jodoctove [Czech], NSC 58809, S 9, BRN 0741934, iodoacetic acid ethylester, ethoxycarbonylmethyl iodide, Ethylester kyseliny jodoctove, iodo-acetic acid ethyl ester, WLN: I1VO2, SCHEMBL145800, 242934_ALDRICH, AC1L1Z16, AC1Q34T8, CTK5B4925, MolPort-003-928-420, Acetic acid, 2-iodo-,ethyl ester, NSC58809, NSC-58809, ZINC01689384, AKOS005068284, AK129912, AN-46773, KB-77223, LS-12280, FT-0625781, 4-02-00-00535 (Beilstein Handbook Reference), I14-101662

Removed Synonyms

Acetic acid, ethyl ester, Iodoacetic acid ethyl ester, Carbonocyanidic acid, ethyl ester, CID12183

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