In 50 g of ethanol were dissolved 2.5 g of sodium metal and 20.0 g of the above ethyl β-(3,3,3-trichloropropyl)isovalerate were added to the solution. The mixture was refluxed for 8 hours. The reaction mixture was neutralized with a solution of hydrogen chloride in dry ethanol and concentrated to about one-twentieth of its original volume. To this concentrate were added 100 g of ice-water and the mixture was extracted with diethyl ether. The ethereal layer was dried over anhydrous magnesium sulfate and distilled to remove the low-boiling fraction. By the above procedure there were obtained 13.7 g of ethyl β-(3,3-dichloroallyl)isovalerate (ethyl 6,6-dichloro-3,3-dimethyl-5-hexenoate), the NMR spectrum of which is given below (yield: 79%).
