Ethanol → Ethyl 4-chloroacetoacetate

HRID 2418662Notes

Reaction equation

HRID 2418662 reaction equation
C=C1OC(=O)C1.ClCl.[Cl:9][CH2:10][C:11](=[O:16])[CH2:12][C:13](Cl)=[O:14].[CH2:17]([OH:19])[CH3:18]>C(Cl)Cl>[CH2:17]([O:19][C:13](=[O:14])[CH2:12][C:11]([CH2:10][Cl:9])=[O:16])[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 12661DiketeneHCID 24526Chlorine2×HCID 30162624-Chloro-3-oxobutyryl chloride

Product 1

HCID 69484Ethyl 4-chloroacetoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A reactor having interior enameling, a total capacity of 630 liters, an effective capacity of 500 liters and a cooling surface of 2.73 m3, was charged with 500 liters of a 15 weight-percent solution of diketene in methylene chloride, and cooled to -20° C. During a period of about 6 hours, a total of 82 kg of chlorine gas was fed into the reactor. The addition of the chlorine gas was in such a way that the temperature at no time rised above -10° C. The reaction mixture was stirred by means of an impeller during the entire time. To the γ-chloroacetoacetic acid chloride a equimolar quantity of ethyl alcohol was added to form the corresponding γ-chloroacetoacetic ethyl ester. The total reaction time was about two hours. The unreacted excess of chlorine and the methylene chloride were removed by distilling them off. A gas chromatographic analysis showed a yield of:

Workup

  1. customA reactor having
  2. customrised above -10° C

Sources & evidence

ORD record
ord-b31a4f27e2b44d64903af2e715dcfe15
Source dataset
uspto-grants-1984_09
Patent number
US04473508

Reaction notes

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