Hydrochloric Acid → Acetic acid, 2-chloro-, 2-chloro-2-oxoethyl ester

HRID 1659437Notes

Reaction equation

HRID 1659437 reaction equation
Cl[CH2:2][C:3]([Cl:5])=[O:4].[C:6]([OH:10])(=[O:9])[CH2:7]O.Cl.S(Cl)([Cl:14])=O>>[Cl:14][CH2:7][C:6]([O:10][CH2:2][C:3]([Cl:5])=[O:4])=[O:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 6577Chloroacetyl chlorideHCID 24386Thionyl Chloride

Product 1

HCID 54510869Acetic acid, 2-chloro-, 2-chloro-2-oxoethyl ester

Procedure

The reactant chloroacetoxyacetyl chloride was prepared by the following intermediate step. A solution was made by mixing 127 grams (g) of chloroacetyl chloride and 57 g of glycolic acid. This mixture was refluxed for two hours. When the evolution of hydrogen chloride ceased the mixture was stripped. The residue was then refluxed for two hours with thionyl chloride. The product was distilled under a water aspirator and fractioned between 105° and 115° C. A yield of 48 g (37%) was obtained. The structure was confirmed by IR, NMR, and mass spectrometry.

Workup

  1. temperatureThis mixture was refluxed for two hours
  2. distillationThe product was distilled under a water aspirator
  3. customfractioned between 105° and 115° C
  4. customA yield of 48 g (37%) was obtained

Sources & evidence

ORD record
ord-a11885f67dba42ccad9bf7c9b5af4c9a
Source dataset
uspto-grants-1981_12
Patent number
US04303792

Reaction notes

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