264 BACON. 



Fifty grams of champaca oil (soluble in 70 per cent alcohol, ester number 

 180) were saponified with 10 grams potassium hydrate in 100 cubic centimeters 

 of 95 per cent alcohol. After heating for one hour with a reflux condenser, 

 two volumes of water were added; 4.5 grams of an amorphous solid separated. 

 This was filtered and the filtrate was separate into neutral, acid, and phenol 

 fractions. By saponification the champaca oil loses all of its characteristic odor, 

 which therefore must be due to esters. 



The phenol fraction (1.5 grams) proved to consist principally of iso-eugenol, 

 as benzoyl iso-eugenol melting at 103° could be obtained from it. The total 

 acid fraction weighed 15 grams. None of this acid boils below 140° at 40 milli- 

 meters; hence there is no methyl ethyl acetic acid. No acids have as yet been 

 identified. 



The neutral portion weighed 23 grams and had an odor somewhat similar to 

 that of oil of bay. 



Some studies were made on the solid which crystallizes from the 

 freshly prepared oil. This substance, as first separated from champaca 

 oil, is of a greenish color and possesses a faint, but pleasant odor. It 

 is readily soluble in. chloroform, acetone, acetic acid, hot alcohol or 

 benzene. It is almost insoluble in ether or petroleum ether. It was 

 purified by repeated solution in hot benzene or chloroform and precipita- 

 tion with ether or petroleum ether. A very peculiar phenomenon was 

 noted during the purification. Many times, without apparent reason, 

 the solution in benzene or chloroform would, with a loud, crackling noise, 

 solidify to a horn-like jelly which was proved to be insoluble in all 

 solvents, and it was impossible to regenerate the original body from 

 this substance. Considerable quantities of the solid were lost in this 

 manner and no method of preventing this polymerization ( ?) was 

 . discovered. 12 



The crystalline solid, after repeated crystallization from benzene and 

 petroleum ether, forms odorless, white needles. 



Eight grams were dissolved in a benzene-alcohol mixture and shaken with a 

 concentrated solution of sodium bisulphite. A precipitate was formed which was 

 filtered. The filtrate was evaporated to crystallization and 4.5 grams of a body 

 obtained, which, after recrystallization from chloroform and ether, melted at 

 165° to 166°. Combustion of this substance gave the following results: 



I. 0.2496 g. gave 0.1587 g. H 2 and 0.5985 g. CO,. 



II. 0.2486 g. gave 0.1593 g. H,0 and 0.5990 g. C0 2 . 



Calculated for Found 



Ci 6 H 2 ii0 5 . i j j 



per cent. per cent. per cent. 



('= 65.7 <i">. 70 65.40 



H= 6.8 7.12 6.80 



Molecular weight 292 



3 - Doctor Freer informs me that in working with acrylic acid several years 

 ago he had a similar experience. 



