184 



0.1 i in of S-4-(liphrniiJ-o-j>ip('nil — ,^ "•''.'/- A 2-kr^>-/i-//('.(V'Hr'. 



This oxim is prepared iii an analogous method to tliat described pre- 

 viously for the preparation of oxims. Wlien recrystallized from a mixture 

 of alcohol and ligroiu, crystals are formed melting at 190-1°. It is soluble 

 in liot alcohol, cold ether, chloroform, and liot benzene, and is insoluble in 

 ligroin (40-60°. ) 



Calculated as C25H21O4N. Found. 



N 3.51 



3.78 



IV. ADDITION OF CUMIXOIN TO BENZALACETOXE' 



3-4-diriimiil-.')-ph('niil-4-(>.rii-i\2-^''f'>-J^-^i''->-'''''' ■ 

 CH. C„H, 



(CH3)oCII.C6H4 .C. (OH) 



(CH3)c.CH.C,H, .C 



CH, 



CO 



CH 



Cuminoiu, in general, reacts less rapidly than benzoin and the yields 

 of /\2~^f'^o~R~^^^^^^6 derivatives are poorer. 



One molecule (6 gr. ) of pure cuminoin'^ and one molecule (3 gr.) of pure 

 benzalacetone dissolved in hot absolute ethyl alcohol (60cc. ) are treated 

 with a solution ((ice.) of sodium ethylate (.5 gr. sodium in 30cc. absolute 

 alcohol). Upon the addition of the sodium ethylate, the mixture turns 

 deep red, and after standing for six hours clusters of needles separate. By 

 recrystallizing twice from glacial acetic acid, pure 3— l-dicumyl-5-phenyl- 

 4-oxy-^2-keto-R-hexene is obtained. It melts at 214°. It is soluble in 

 cold acetic ether, chloroform, hot benzene and ligroin (110-120°); insoluble 

 in cold alcohol, ligroin (40-60°), and ether. The yield is about 27% of tlie 

 theoretical. 



Calculated as C3„H3 20. Found. 



C 84.90 84.77 



H 7.54 7.83 



Dissertation, Chicago, 1897, p. 19. 

 Beriehte, XXVI, 64. 



