( 467 ) 



By saponification of lupeol benzoate with alcoholic- potassium 



hydroxide and recrystallisation from alcohol or acetone, the lupeol 



was obtained in the form of fine, long needles m.p. 211°, (corr. 215°). 



Found: C 84.62 84.65 84.40 84.50 Calculated for C 81 H so 84.85 



H 11.78 11.93 11.82 12.02 11.49 



Md = +- ^7°,2 in chloroform. 



In the first place it seemed to me of importance to ascertain 

 whether double bonds occur in lupeol. Therefore, a solution of 

 lupeol in carbon disulphide was treated with a solution of bromine 

 in the same solvent. Hydrogen bromide was evolved. By recrvstal- 

 lising the reaction product from methyl alcohol, needles containing 

 1 mol. of the latter are formed. The melting point of this substance, 

 dried at 100', was 184°, (corr. 185°). 

 Found: I II III IV V VI VII calc. for C 81 H 49 OBr. 



C 72.14 72.30 71.90 



H 10.2610.07 Camus Liebig 9.55 



Br UAïTuIo 15Ml^6flZQl 15.45 



[«] D = -}- 3°, 8 in chloroform. 

 Most probably, a monosubstitution product had formed and I now 

 tried to obtain an additive product of the benzoate. When dissolved 

 in a mixture of glacial acetic acid and carbon disulphide and then 

 treated with a solution of bromine in glacial acetic acid, it yielded, 

 after spontaneous evaporation of the carbon disulphide, beautiful 

 leaflets. On extracting this product with boiling acetone a less easily 

 soluble substance was left, which proved to be a monobromide. After 

 repeated recrystallisation from aethyl acetate, I obtained fine, thick 

 crystals which when melting were decomposed. Placed in the bath 

 at 240° it melted at 243?. 

 Found I II III IV V VI VII VIII IX X 



C 72.62 72.90 72.58 72.46 72.59 



H 8.85 8.88 8.72 9.09 8.84 Carius Liebig 



Br 13.14 13.04 12.97 13lol^01 



Calculated C J8 H„ 0, Br, C = 73.38, H = 8.61, Br = 12.87. 



[«] D = -f- 44°, 9 in chloroform. 



The bromine atom is contained in the lupeol nucleus, because on 

 saponification an alcohol containing bromine, and benzoicacid are formed. 



The more readily soluble portion crystallises from acetone in 

 beautiful leaflets. It is also a monobromide but could not with 

 certainty be characterised as a chemical individual. 



One of the means to trace the structure of a substance is the 

 gradual destruction by oxidation. 



