Synthesis of ethyl chloroacetate

Preparation of ethyl chloroacetate

Ethyl chloroacetate is prepared by the action of ethyl alcohol on monochloroacetic acid in presence of sulfuric acid.

Preparation of ethyl chloroacetate

Preparation of ethyl chloroacetate

To the round bottom flask fitted with a reflux condenser and stirrer 75 g of monochloracetic acid, 45 g of 95% ethyl alcohol and 10 g of concentrated sulfuric acid are added. The reaction flask is gently heated at 100° C and refluxing was continued for about 5-6 hours. At the end of the reaction the flask is allowed to cool and then poured into a separatory funnel containing cold water. The ethyl chloroacetate layer is separated, washed several times with water, dried with calcium chloride and then fractionally distilled by collecting the fraction passing over between 40.5-45.0° C. Ethyl chloroacetate is a colorless liquid having an odor of fruit and boils at boiling at 143.5° C. It is insoluble in water, but easily soluble in the common organic solvents.

The war gases chemistry and analysis, by M. Sartory, 118, 1939

IUPAC Name

ethyl 2-chloroacetate

InChI

InChI=1S/C4H7ClO2/c1-2-7-4(6)3-5/h2-3H2,1H3

InChI Key

VEUUMBGHMNQHGO-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)CCl

MeSH Synonyms

EMCA, ethyl monochloroacetate, monochloroacetic acid ethyl ester

Depositor-Supplied Synonyms

ETHYL CHLOROACETATE, Ethyl chloracetate, 105-39-5, ethyl 2-chloroacetate, Ethyl monochloroacetate, Chloroacetic acid ethyl ester, Acetic acid, chloro-, ethyl ester, Ethyl chloroethanoate, Ethyl monochloracetate, NSC 8833, 2-Chloroacetic Acid Ethyl Ester, Ethyl alpha-chloroacetate, Acetic acid, 2-chloro-, ethyl ester, UNII-6H07TEH4TF, Ethyl .alpha.-chloroacetate, Chloroacetic acid, ethyl ester, Ethylester kyseliny chloroctove, CCRIS 7747, HSDB 408, VEUUMBGHMNQHGO-UHFFFAOYSA-N, EINECS 203-294-0, UN1181, Ethylester kyseliny chloroctove [Czech], BRN 0506455, AI3-19743, Ethyl-2-chloroacetate, Ethyl |A-Chloroacetate, ethyl 2-chloroethanoate, ACMC-1BVYE, AC1L1PGX, Ethyl 2-Monochloroacetate, DSSTox_CID_6715, AC1Q34SC, 6H07TEH4TF, DSSTox_RID_78196, DSSTox_GSID_26715, SCHEMBL59424, E16856_ALDRICH, KSC492K1T, chloro acetic acid ethyl ester, chloro-acetic acid ethyl ester, (Ethoxycarbonyl)methyl Chloride, 240710_ALDRICH, CHEMBL3186148, Ethyl ester of chloroacetic acid, 24540_FLUKA, CTK3J2519, NSC8833, 2-Chloro-acetic Acid Ethyl Ester, MolPort-001-781-436, BB_SC-6777, NSC-8833, Tox21_201053, ANW-15212, BBL012578, STL163644, ZINC01648258, AKOS000118975, MCULE-2200524105, RL00246, RTR-001125, UN 1181, NCGC00248909-01, NCGC00258606-01, AN-24712, BP-21332, CAS-105-39-5, CJ-26634, Ethyl chloroacetate [UN1181] [Poison], KB-77211, LS-11284, Ethyl chloroacetate [UN1181] [Poison], TR-001125, FT-0625769, 83290-EP2270006A1, 83290-EP2277945A1, 83290-EP2305655A2, 4-02-00-00481 (Beilstein Handbook Reference), I14-2542, 3B3-020251, InChI=1/C4H7ClO2/c1-2-7-4(6)3-5/h2-3H2,1H

Removed Synonyms

Acetic acid, ethyl ester, CID7751, c0092

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1 comment

  1. Zoran r

    passing over between 40.5-45.0° C. Ethyl chloroacetate is a colorless liquid having an odor of fruit and boils at boiling at 143.5°

    40.5-45.0° C or 140.5-145.0° C??????????????????????Zoran

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