Ethanol → Ethyl 4-chloroacetoacetate

Participants

Reaction Conditions

Reaction Steps

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:

Provenance & Evidence