Ethanol → Ethyl 4-chloroacetoacetate

HRID 1863205Notes

Reaction equation

HRID 1863205 reaction equation
[Cl:1]Cl.[CH2:3]=[C:4]1[O:8][C:6](=[O:7])[CH2:5]1.[CH2:9]([OH:11])[CH3:10]>C(Cl)(Cl)(Cl)Cl>[CH2:9]([O:11][C:6](=[O:7])[CH2:5][C:4]([CH2:8][Cl:1])=[O:3])[CH3:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 12661DiketeneHCID 24526Chlorine

Product 1

HCID 69484Ethyl 4-chloroacetoacetateYield 94%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

72 g (1 mol) of chlorine were passed into a solution of 84 g (1 mol) of diketene in dry carbon tetrachloride at -20° C. and the reaction solution was then added dropwise, while stirring, to 200 ml of ethanol, during which addition the temperature was not permitted to exceed 0° C.; the solvent was then stripped off on a rotary evaporator and the residue was distilled. 155 g (94% of theory) of γ-chloroacetoacetic acid ethyl ester of boiling point 90° C./7 mm Hg were obtained.

Workup

  1. additionthe reaction solution was then added dropwise
  2. customto exceed 0° C.
  3. customthe solvent was then stripped off on a rotary evaporator
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-ef86bbfb38b343f58baefe01b5877015
Source dataset
uspto-grants-1979_09
Patent number
US04168304

Reaction notes

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