336 BROOKS. 



Fifteen grams of oil were distilled at 13 millimeters pressure. Up to 190° 

 only 4.5 grams of distillate were obtained. This was collected in four fractions, 

 but these fractions were not investigated as a large part of the sample had 

 poljTnerized. 



The oil obtained by distilling it with steam consists largely of cineol. 

 IVentj^-fiYe gi'ams of oil yielded about 6 grams of distillate Avhich 

 smelled strongly of cineol and also of p-cresol methyl ether. The latter 

 substance as yet has not been identified in this oil. Methyl salicylate, 

 which has a somewhat similar odor, is not present. 



Saponification of the oil with alcoholic caustic potash, distillation of 

 the alcohol, and distillation of the remainder with steam, yields a dis- 

 tillate amounting approximately to 25 per cent of the original oil. 

 This distillate consists largely of cineol as the fraction boiling from 172° 

 to 178° on treatment with iodol gave the double compound melting at 

 112° to 114°, which is characteristic of cineol. No other compounds 

 have been identified in these fractions. 



Fifty grams of champaca oil were shaken with a concentrated solution of 

 of sodium acid sulphite. On adding sodium carbonate to the sulphite solution 

 and extracting with ether, 3.0 grams of oil were obtained which smelled strongly 

 of benzaldehyde. A semicarbazone was prepared which melted at 195° to 200°, 

 not sharp, and a phenyl-hydrazone which after reerystallizing from dilute alcohol 

 melted at 149° to 151°. Benzaldehyde, therefore, is present, but another sub- 

 stance also is present which has not been identified. 



One hundred grams of the oil were dissolved in alcohol and precipitated in 

 fractions, by the addition of water. The first fractions contained most of the 

 cineol. . The last fractions to be separated in this manner had an altogether dif- 

 ferent 'odor from the first. Finally, extraction of the aqueous alcoholic solution 

 with chloroform yielded a heavy oil which contained benzyl alcohol. The presence 

 of benzyl alcohol was shown by shaking out with sodium acid sulphite in order 

 to remove any aldehydes present and then oxidizing 0.5 cubic centimeter of the 

 oil with chromic acid mixture. On distilling ^^^th steam and adding one drop 

 of phenylhydrazine to the distillate, benzaldehyde phenyl-hydrazone was obtained, 

 which, after reerystallizing from dilute alcohol, melted at 153° to 154°. 



Saponification of 10 grams of the last fraction precipitated by water yielded 

 1 .6 grams of an acid tar, which, on boiling with water, yielded 0.3 gram of 

 benzoic acid crystals, melting sharply at 120°. The melting point was unchanged 

 when the substance was melted with pure benzoic acid. 



No acids other than benzoic acid have as yet been identified. Acetic or formic 

 acid is not pi'esent. 



Fifty grams of oil were saponified in the usual manner, and after the neutral 

 and phenolic constituents had been removed the solution was acidified and ex- 

 tracted five times with ether. The solution was then distilled with steam until 

 one-third of it had passed over. This solution required only 1.2 cubic centimeters 



of — caustic soda for neutralization. 



N 



The ether extract contained considerable resin. After purifying with dilute 



alcohol the acid was obtained as a pungent-smelling oil, very sparingly soluble in 



water. It has not yet been identified. 



