126 BACON. 



262°.4 (standard tliermometer, wholly in tlie vapor). The distillate was yellow 



in color, being somewhat darker than the oil distilled ire vacuo, but no odor, gas 



evolution, or other plienomena which would indicate any decomposition were 



30° 30° 



noted. Tlie constants found were: Specific gravitv, =0.9104; X--- = 1.4960; 



one oAo ' ^ 



A^ = + 116.5; A~= + 120.8. 



The action of bromine on the sesquiterpene was as follows: Some of the body of 

 a constant boiling point was mixed with glacial acetic acid in which it is not very 

 soluble. A violent reaction took place on adding bromine drop by drop, and the 

 liquid turned an intense blue color, later passing into purple. As the sesqui- 

 terpene is completely and easily soluble in chloroform, the next experiment was 

 made while using this solvent. The .same results were obtained. On adding a very 

 dilute, cold solution of bromine in chloroform to a solution of the terpene in 

 chloroform in a freezing mixture, the first few drops were simply decolorized, 

 but very soon the same color changes as have been mentioned above manifested 

 themselves. The brominated sesquiterpene in every instance proved to be a 

 hopeless tar. 



A small amount of sesquiterpene gave no reaction either in the cold or at 

 100° when treated with sublimed aluminum chloride. The oil reacted instantly 

 with warm, acidified potassium permanganate, reducing the permanganate, and 

 giving a tar of a very pleasant odor from which no definite bodies could be 

 isolated. The sesquiterpene when treated with concentrated hydrochloric acid 

 at first gave a pink color which later deepened to an intense purple. Iodine 

 numbers for this sesquiterpene were determined for me by llr. Eeibling and Mr. 

 del Rosario of the Bureau of Science. Working according to the standard Hanus 

 method they found .307, 372, 375, 384 (calculated Hanus number for 01 = 376). 

 The iodine number which was found, depended upon the length of time during 

 which the sesquiterpene remained in contact with the iodine solutions. If these 

 solutions were left standing for twenty-four hours or more, iodine numbers much 

 higher than the above were obtained, namely, 564, 583, etc. These results are 

 probably due to the peculiar, unsaturated, and easily oxidlzable structure of the 

 sesquiterpenes. 



Some of the sesquiterpene isolated as described above and which liad been 

 allowed to stand in a glass-stoppered bottle in the light for one and one-half 

 years was redistilled over sodiiim in vacuo. It gave the following constants: 



Boiling point at 15 millimeters, 130° to 131°; specific gravity, ?_ =0.9100; 



30° 30° 4° 



N2^ = 1.4950; a ^ = 101.2. 



This body was dissolved in an equal weight of dry ligroiu and satur- 

 ated with dry hydrochloric acid. Two molecules of hydrocliloric acid 

 for one molecule of the sesquiterpene were added and the solution 

 became purple. No solid hydrochloride could be obtained and the 

 addition product could not be distilled in vacuo without decomposition. 

 Au attempt was therefore made to subject the crude product to the 

 Grignard reaction in the hope that di- and tetra-hydro sesquiterpenes, 

 at present an imknown series of bodies, might be obtained. The hydro- 

 chloride had a slight action on magnesimn, but as the reaction did not 

 go to completion it was impossible to isolate the compounds wished for. 

 The attempts to prepare these reduced sesquiterpenes, which may tlirow 

 some light on the very dark field of their cliemistry. will be repeated 



