2-Chlorocyclooctanone oxime hydrochloride

B. 2-Methoxycyclooctanone oxime. In a 500-ml., three-necked, round-bottomed flask, fitted with a mechanical stirrer, a dropping funnel, and a reflux condenser equipped with a calcium chloride tube, is placed a solution of 53.5 g. (0.252 mole) of crude 2-chlorocyclooctanone oxime hydrochloride in 250 ml. of methanol. While cooling the vessel with running water, 60.7 g. of triethyl-amine (0.60 mole) is added dropwise during 40 minutes. The reaction temperature is kept below 50° and the reaction is continued for 30 minutes with stirring. After removal of methanol under reduced pressure using an efiicient rotatory evaporator, a light brown semisolid is obtained it is treated with 200 ml. of ether and 200 ml. of water to effect complete solution. The ether layer is separated and the aqueous layer is further extracted twice with ether. The combined ether solution is washed with saturated sodium chloride and dried over sodium sulfate. Removal of ether affords 42.8 g. of crude 2-methoxycyclooctanone oxime (Note 3) as a brown oil. 

Chlorocyclooctanone oxime hydrochloride is unstable to heat. Therefore the temperature during removal of methanol should be kept below 35°. 

A. 2-Chlorocyclooctanone oxime hydrochloride. In a 2-1. threenecked, round-bottomed flask, fitted with a mechanical stirrer, a gas inlet tube, and a tube fitted with a thermometer and a calcium chloride tube, is placed 55 g. (0.50 mole) of freshly distilled cyclooctene and 600 ml. of trichloroethylene. The solution is cooled with ice water to 5°, and 36 g. (0.55 mole) of nitrosyl chloride (Note 1) and excess of hydrogen chloride gas (about 4(K) -600 ml. per minute) are bubbled into the solution, keeping the reaction temperature between 5 10°. The solution gradually... 

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