184 



O.riin of 3-4-diplii'iii/l-o-j>lj><'ri/l — 4 "''.'/-A i-^i'fo-Ii-he.icne. 



Tliis oxim is prepared iu an analogous method to that described pre- 

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

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

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

 ligroin (40-60^) 



Calculated as CasHgiO.N. Found. 



N3.51 



378 



IV. ADDITION OF CUMINOIN TO BENZALACETONE' 



.)-4-0 i(' ti ni iil-.'>--pheniiJ -4-o.nj- l\2-ki't()-Ii-]ii"X('nc . 



CH . C'eHs 



(CH3)2CH.C6H4.C.(0H) 



(CH3).. .CH.CeH^ .C 



CH, 



CO 



CH 



Cuminoin, in general, reacts less rapidly tlian benzoin and the yields 

 of A,2~1^6to-E<-hexene derivatives are poorer. 



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

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

 VPith a solution (6cc.) 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 3-4-dicumyl-5-phenyl- 

 4-oxy-A2-J^6to-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. 

 » Berichte, XXVI, 64. 



