YLANG-YLANG OIL. 85 



SUMMARY OF RESULTS. 



Ylang-ylang oil is thus seen to contain the following substances: 

 PormiCj acetic, valerianic (?), benzoic and salicj^lic acids, all as esters; 

 methyl and benzyl alcohols ; pinene and other terpenes, linalool, geraniol, 

 safrol, cadinene and other sesquiterpenes ; eugenol, isoeugenol, |j-kresol, 

 probably as methyl ethers ; and kreosol. 



Many of the esters which could possibly be formed by a combination 

 of the isolated alcohols and acids have been prepared in this laboratory in 

 order to become familiar with their properties and especially with their 

 odor. It seems of interest to give notes in regard to their properties. 



Benzyl salicylate. — No record appears in the literature of tlie preparation of 

 this compound. It is made as follows : 27.4 grams of salicylic acid are neutralized 

 with 11.2 grams of potassium hydroxide and the solution evaporated to dryness. 

 This potassium salt is heated to 200° for four hours in sealed tube with 25 

 grams of salicylic acid and 25.2 grams of benzyl chloride. On opening the tube 

 no pressure is observed and all of the benzyl chloride has disappeared. There is 

 obtained 26 grams of a colorless, viscous oil boiling between 186° and 188° at 10 

 millimeters. The odor is slightly aromatic and pleasant, but not powerful. The 

 oil, after three months in the ice box, has not solidified. Five grams of the 

 ester saponified with alcoholic caustic potash, gave 2.4 grams of salicylic acid 

 melting at 155° ( recrystallized from water), and the acid was further identified 

 by conversion into the methyl ester. There also resulted 2 grams of benzyl 

 alcohol, boiling at 204° and converted into benzyl acetate. 



Bensyl henzoate has been prepared by the action of sodium benzylate on 

 benzaldehyde. The method used in this laboratory was as follows : 50 grams of 

 sodium benzoate, 50 grams benzoic acid, and 43 grams of benzyl chloride were 

 heated on a reflux condenser in a metal bath at a temperature of 200° for two 

 hours. There resulted 46 grams of oil boiling between 315° and 320°. Benzyl 

 valerianate and benzyl butyrate were also prepared by the same general method, 

 the yield being very good. The method formerly in use, which employed the lead 

 salts, did not give good results. 



Benzyl valerianate can also be prepared in almost quantitative yield bj' the 

 action of valeryl chloride on sodium benzylate. The properties of this body 

 correspond to those given in the literature. The odor of this ester is not as 

 sweet as is that of benzyl acetate, it being more like that of fruit. It is almost 

 certain that there are traces of benzyl valerianate in ylang-ylang oil. 



Benzyl-methyl ether is obtained in almost quantitative yield by heating benzyl 

 chloride with a slight excess of sodium methylate dissolved in methyl alcohol, 

 in a sealed tube to 120° for two hours. The transformation is not complete if 

 these same substances are heated only in an oil bath on a reflux condenser, and 

 in addition the benzyl-metliyl ether always contains chlorine. . 



Benzyl-methyl ether is a colorless oil boiling between 166° and 168°; it has 

 an almost nauseatingly sweet odor. There is probably a veiy small amount of it 

 present in ylang-ylang oil. 



Benzyl formate. — Benzyl chloride is heated with a slight excess of potassium 

 formate dissolved in formic acid in a sealed tube at 140° for two hours. The 

 body boils at 84° to 85° at 10 millimeters pressure and has an odor sweeter than 

 that of benzyl acetate, but much like it. The yield is over 90 per cent by this 

 method. It is necessary to use a sealed tube, as benzyl chloride does not dissolve 

 in absolute formic acid at 100°. 



