Isopropanol → Isopropyl dichloroacetate

HRID 1165268Notes

Reaction equation

HRID 1165268 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[CH:7]([OH:10])([CH3:9])[CH3:8]>>[Cl:1][CH:2]([Cl:6])[C:3]([O:10][CH:7]([CH3:9])[CH3:8])=[O:4]

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 6593Dichloroacetyl chloride

Product 1

HCID 90683Isopropyl dichloroacetate

Procedure

9 g. (60 mMole) Dichloroacetyl chloride are added dropwise to 20 g. isopropanol cooled to 3° C. in an ice/water bath. The reaction solution is further stirred for 30 minutes at ambient temperature, whereafter excess alcohol is removed in a vacuum at ambient temperature. The residue is subsequently mixed with a mixture of ice water and dichloromethane. After separation of the phases, the organic phase is successively washed with water, aqueous sodium hydrogen carbonate solution and again with water and dried over anhydrous sodium sulphate. After removal of the solvent, there are obtained 7.5 g. (73% of theory) isopropyl dichloroacetate which, after distillation (67°-68° C., 24 hPa) is obtained as a colourless liquid.

Workup

  1. customis removed in a vacuum at ambient temperature
  2. additionThe residue is subsequently mixed with a mixture of ice water and dichloromethane
  3. customAfter separation of the phases
  4. washthe organic phase is successively washed with water, aqueous sodium hydrogen carbonate solution and again with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customAfter removal of the solvent, there
  7. customare obtained 7.5 g
  8. distillation(73% of theory) isopropyl dichloroacetate which, after distillation (67°-68° C., 24 hPa)
  9. customis obtained as a colourless liquid

Sources & evidence

ORD record
ord-09fc2ff9507c4860b8a24e7d887a717b
Source dataset
uspto-grants-1990_03
Patent number
US04908385

Reaction notes

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