( 468 ) 



The lupeol was, therefore, oxidised with t he Kiliani mixture 1 ). 

 Lupeol dissolved in benzene was shaken with a weighed quantity 

 of die oxidising liquid, 6 atoms of oxjgen calculated for 1 mol. of 

 lupeol. Titrations of the oxidising liquid with potassium iodide and 

 sodium thiosulphate showed, that after six hours one atom of oxygen 

 had heen consumed and as the amount of chromic acid did not 

 diminish any further, this one atom had been taken up quantitatively. 

 The oxidation product, which crystallised from alcohol in beautiful, 

 thick needles, melted at KJO 1 (corr. 170°) and proved to be a ketone, 

 to which I gave the name of lt//>r<>,i. 



Found (' 84.05 84.1)1 85.07 84.7(1 ('ale. for C 8l H 48 85.24 



II 11.(54 11.81 11.62 L1.6J 11.59 11.09 



[a] u == -f 63°,1 in chloroform. 



Dr. Jaeger was kind enough to examine the crystalform of the 

 lupeon. It belongs to the rhombo-bipyramidal class. A complete 

 description will appear elsewhere. 



With hydroxylamine an oxime of the lupeon was obtained, which 

 is bul little soluble in alcohol. 



Recrystallised from ethyl acetate, it forms white, soft, light needles, 

 which are decomposed when melting. Placed in the bath at 278°, 

 they melt at 278°, 5. 

 Found C 81.98 Calc. for C„ H 48 NOH 82.41 



II 11.44 with lead chromate 10. .'4 



X ~~Jos" 3.11 



«]n = -J- 20\5 in chloroform. 



Bromine dissolved in glacial acetic acid added to a solution of 

 lupeon in the same solvent gave hydrogen bromide and a dibromide, 

 which was deposited from the acid. Recrystallised from a mixture 

 of benzene and glacial acetic acid it consisted of beautiful, hard 

 needles, which were decomposed when melting. Placed in the bath at 

 253 c the melting point was 254°. 

 Found I II III IV V VI VII VIII IX X 



C 62.31 62.71 62.50 62.30 



11 8.13 8.26 8.05 8.06 Carius Liebig 



Br 26.88 201 27.08 26.85 27.35 27.23 



Calc. for C 81 H 4 „ Br„ C = 62.58, H = 7.80, Br = 26.90. 

 [«] D = -f- 21°,4 in chloroform. 



When dissolved in ether, lupeon gave with hydrogen cyanide 

 under the influence of a trace of ammonia a cyanohydrin, which 



i) Ber. 34. 35lii (1901). 



