Ryan and Nolan — On Higher Ketones and Secondary Alcohols. 3 



and decomposed by addition of a solution of ammonium chloride in iced water. 

 The ketone was extracted with ether, and after removal of the latter by 

 distillation the residue was boiled for about an hour with alcoholic potash, 

 and then evaporated to dryness. Petroleum ether extracted about one 

 gramme of methylpentadecyl ketone from the dry residue. 



The ketone is readily soluble in chloroform, benzene, or ether, moderately 

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

 hot, alcohol from which it crystallizes in plates which melt at 48°C. 



The compound previously obtained by Krafft's method {loc. cit.) also 

 melted at 48-C. 



Phenylpenfadeci/l Ketone CsHsCOCisHsi. — On addition of 6'2 grammes of 

 powdered palmitamide to the Grignard reagent prepared by dissolving 1'44 

 grammes of magnesium in a solution of 9 '5 grammes of bromobenzene in 

 2o c.c. of ether a considerable evolution of heat was observed. The mixture 

 was allowed to remain at the laboratory temperature for three days, and was 

 then warmed for a few hours, cooled, and decomposed by a solution of ammonium 

 chloride. The ketone was extracted with ether, the solvent removed, and 

 the residue was then freed from diphenyl by distilling the latter over in a 

 current of steam. Unchanged amide was removed by evaporating to dryness 

 with alcoholic potash and extracting the ketone from the residue with 

 petroleum ether. It was decolorized by means of animal charcoal, and 

 recrystallized from alcohol. The yield of pure ketone was 50 per cent. 



Phenylpentadecyl ketone crystallises in plates which melt at 59'C. It is 

 easily soluble in chloroform, benzene, ether, or warm alcohol, but is only 

 sparingly soluble in cold alcohol. 



Phenylpentadecyl Ketoxime was prepared by heating 0"8 gramme of the 

 ketone with an equal weight of hydroxylamine hydrochloride and 1"2 gramme 

 of potash in diluted alcohol for two hours. The mixture was acidified with 

 acetic acid, diluted with water and extracted with ether. On distilling the 

 ether a residue, which was insoluble in potash, was obtained. It crystallized 

 from alcohol in needles which melted at 73-74°C. 



0-2072 g. substance gave 8'4 c.c. N at 21-5"C and 769 mm. p. X = 4-6, 



C20H37XO requires N = 4-'23. 



Phenylpentadecyl ketoxime is soluble in warm alcohol, chloroform, 

 benzene, or ether, and is only slightly soluble in cold alcohol or petroleum 

 ether. 



p-Tolylpentadecyl Ketone GHsCeHiCOCisHs,. — By a method of preparation 

 analogous with that just described, a yield of 60 per ceut. of the pure ketone 



[^2J 



