Hydrochloric Acid → 1-Chloro-4-carbomethoxy cyclohexane

Temperature

22 °C

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%).

1. additionwas added over a period of about 0.5 hours
2. customrose exothermically to about 34° C
3. additionDuring the addition
4. temperatureto reflux condition (about 40° C.)
5. temperatureThe reaction mixture was then maintained under a nitrogen atmosphere
6. stirringwith stirring, for about 16 hours at ambient conditions
7. customThe crude reaction product
8. washwashed with methylene chloride
9. distillationdistilled
10. customto yield

ORD record

ord-0a3b4868c83541a398d89ec083c5ebff

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04792618