Ryan and Nolan- — On Higher Ketones and Secondary Alcohols. 5 



The ketone is easily soluble in chloroform, benzene, ether, or hot alcohol, 

 fairly soluble in acetone or petroleum ether, and slightly soluble in cold 

 alcohol. 



Ethylheptadecyl Ketone CaHsCOCnHso- This ketone was got by acting on 

 stearamide with ethyl magnesium iodide, but the yield was a poor one. 



It is easily soluble in benzene, ether, chloroform or hot alcohol, from 

 which it crystallizes in plates which melt at 57° C. 



0-2308g. substance gave 0-6854g.(;O2 and 0-2746 g. HjO. C = 80-99, H = 13-32. 



CjoHioO requires C = 81-08, H = 13-51. 



Phenylheptadecyl Ketone OsHsCOCnHss. The preparation of phenylheptadeeyl 

 ketone from phenyl magnesium bromide and stearamide was analogous with 

 that of phenylpentadecyl ketone. The yield of the ketone was good. 



Phenylheptadeeyl ketone crystallizes in plates which melt at 64°0., and 

 are easily soluble in chloroform, ether, or hot alcohol. 



Its lyhenylhydrazone, which was obtained from the alcoholic solution of the 

 components, crystallizes in needles which melt at 54° C. 



0-1791 g. substance gave 10-4c.c.N at 20°C. and 758 mm. p. N = 6-62 



GsoHieNj requires N = 6-45 



p-Tolylheptadecyl Ketone CHsCsHiCOCnHas. p-Tolylheptadecyl ketone, 

 which was obtained from p-tolyl magnesium bromide and stearamide, is 

 easily soluble in chloroform or ether, fairly soluble in benzene or acetone, 

 and slightly soluble in cold alcohol or petroleum ether. It melted at 

 66°-67°C. 



a-Naphthylheptadecyl Ketone CioH7COCnH35. By interaction of a-naphthyl 

 magnesium bromide and stearamide in ethereal solution o-naphthylheptadecyl 

 ketone was prepared. It crystallized from alcohol in long curved needles 

 which melted at 53-54° 0. 



0-1676 g. substance gave 0-5260 g. CO2 and 0-1620 g.H^O C = 85-59, H = 10-74 



Cj^HjjO requires C = 85-28, H = 10-66, 



o-Naphthylheptadecyl ketone dissolves readily in chloroform, benzene, 

 ether, or hot alcohol. 



An attempt to prepare the phenylhydrazone of this ketone was unsuccessful,, 

 probably owing to a steric hindrance similar to that exhibited in its attempted- 

 preparation by Pinner' of the imino-ether of a-naphthoic nitrile. 



1 Bar. xxiii (1890), p. 2918. 



