86 BACON. 



Geraniol-methyl ether. — This body was prepared from the sodium derivative 

 of geraniol and methyl iodide. It is a colorless oil, boiling between 100° and 

 105° at 10 millimeters and at 208° to 212° at ordinary pressure. Its odor 

 resembles that of geraniol, but it is more like that of grass. 



Linalo6l-7nethyl ether is prepared in the same manner as geraniol-methyl ether, 

 it boils between 1S9° and 192°, and its odor is not very different from that of 

 linalool, it is not as fragrant as that substance. 



Geraniol bengoate was prepared by the Baumann-Schotten method, using 10 

 grams of geraniol and 10 grams of benzoyl chloride. The oil boils between 198° 

 and 200° at 15 millimeters. It has quite a pleasant odor, much like that of some 

 of the higher boiling fractions of ylang-ylang oil. 



SYNTHESIS OF YLANG-YLANG OIL. 



An attempt was made to prepare an artificial product to test the ac- 

 curacy of these studies on the composition of ylang-ylang oil. The fol- 

 lowing substances were used : 



Methyl benzoate; benzyl acetate and formate; benzj-l methyl ether (trace) ; 

 benzyl valerianate (trace) ; methyl .salicylate; benzyl benzoate; cadinene; safrol; 

 isoeugenol-methyl ether; eugenol; kreosol; methjd anthranilate (trace) ; p-kresol- 

 methyl ether; p-kresol acetate. 



With these ingredients a mixture was compounded smelling deceptively 

 like good ylang-ylang oil. The fluorescence of ylang-ylang oil, wliich 

 is always present to a greater or lesser degree, is probably due to the jsres- 

 ence of methyl anthranilate. 



The above work, and that of others demonstrates that jdang-ylang oil 

 has a composite odor, derived from that of man}^ constituents. Wliile it 

 is possible to make a very good artificial ylang-ylang oil, I do not believe 

 that distillers of the best quality of ylang-ylang oil have much. to fear 

 from this competition, as the odor of a first-class oil seems to \igve more 

 permanence than that of the artificial product. This is a result, I 

 believe, of the presence of sesquiterpene alcohols and fragrant resins in 

 the former. 



Work on the physical constants and metliods of analysis of ylang-ylang 

 oil will be continued as fast as material is available. The future de- 

 terminations, in addition to the constants given in this paper will include 

 the acetyl number, and if possible a phenol number. The acetyl number 

 is undoubtedly of much importance, as is evidenced from the large 

 percentage of fragrant alcohols found in ylang-jdang oil. Our fnst 

 quality of oil gave an acetyl number of 74, while a second cpality only 

 gave one of 42. We will also in our future work use a constant ec[ual 

 to the sum of the ester and acetyl numbers, thus representing the total 

 amount of alcohols and esters in the oils. Such a number for the last 

 mentioned first quality oil was 174 as compared to 110 for the second 

 grade product. We believe we will thus be able from a few simple ana- 

 lytical determinations to draw many conclusions as to the composition of 

 any ylang-ylang oil presented to us and thus be able to judge of its 

 quality. 



