Hydrochloric Acid → 1-Chloro-4-carbomethoxy cyclohexane

Participants

Reaction Conditions

Reaction Steps

A mixture of 200 parts of anhydrous aluminum chloride in 2000 parts of methylene chloride was maintained under an atmosphere of nitroge while 129 parts of methyl acrylate was added over a period of about 0.5 hours. With the addition of the methyl acrylate, the temperature of the mixture rose exothermically to about 34° C. The mixture was cooled to about 22° C. and 132.8 parts of freshly prepared chloroprene was added slowly, with stirring over a period of about 1.5 hours. During the addition, the temperature rose slowly to reflux condition (about 40° C.). The reaction mixture was then maintained under a nitrogen atmosphere, with stirring, for about 16 hours at ambient conditions. The crude reaction product was then treated with 10% HCl, and washed with methylene chloride and distilled to yield an essentially pure mixture of 1-chloro-4-carbomethoxy cyclohexene (92%) and its isomer 1-chloro-5-carbomethoxy cyclohexene (8%).

Provenance & Evidence