106 Report of Schimmel $ Co. April 1913. 



derived from the said alcohol and the acid C15H24O2. According to the most recent 

 investigations, which have been conducted by F. W. Semmler, F. Risse, and F. Schroter 1 ), 

 the formulas given by Genvresse and Langlois are incorrect, the proper notations being, 

 for vetivenol C15H24O and for the acid Ci 5 H 22 2 . The last-named investigators examined 

 an oil distilled by us, and possessing the following properties: d 20 o 1,0239, « D -[-31 , 

 r»D2oo 1,52552. They first resolved 400 grams of this oil, at 12 mm., into the following 



four fractions: — .. n A ^ A ^ n . nn 



A) B.p. 129 to 175°, 23 p. c. 



B) B.p. 170 to 190°, 34 „ „ 



C) B.p. 190 to 250°, 8 „ „ 



D) B.p. 250 to 300°, 30 „ „ 



Fraction D, when subjected to further distillation, was split up into two portions, 



as follows: — 



D,a) B.p. 138 to 260° (13 mm.), 28 p. c. 



D,b) B.p. 260 to 298° (13 mm.), 62 „ „ 



Analysis showed beyond doubt that the portion D, b consisted of an ester C30H44O2 

 of the acid C L r>H2>0 2 and the alcohol C15H24O. The characters of the free alcohol 

 are as follow: b.p. 170 to 174° (13mm.), d 20 o 1,0209, « D + 34°30', n D 1,52437, mol.refr. 

 found 65,94, calc. for Ci 5 H 24 0/ = 66,00. Hence the vetivenol of this fraction can only 

 be a tricyclic, simply unsaturated alcohol. The acid Ci 5 H 22 2 boils at 202 to 205° 

 (13 mm.), is tricyclic, and is called vetivenic acid by the authors. Its methylester boils 

 between 170 and 173° (18mm.): d, o 1,0372, « D + 42° 12', n D 1,50573, mol. refr. found 71,05, 

 calc. for C 16 H 2 4 2 r 71,31. 



Fractions A and B, when subjected to repeated fractional distillation in vacuo 

 yielded a fraction boiling between 173 and 180° (13 mm.), from which vetivenol was 

 obtainable by treatment with phthalic anhydride. It therefore appears to be a primary 

 alcohol. Tricyclic vetivenol is capable of being reduced to tricyclic dihydrovetivenol, 

 Cir,H 26 by means of hydrogen in the presence of platinum: b. p. 176 to 179° (17 mm.), 

 d 20 o 1,0055, « D ^-31Q t n D 1,51354. Vetivenol (tricyclic) yields an acetate, b.p. 180 to 

 184° (19 mm.); d 20 o 1,0218; « D + 28° 48'; n D 1,50433; mol. refr. found 75,91, calc. for 

 C17H26O2/ 75,61. Fraction C, upon saponification, yielded an oil from which, under 

 repeated distillation, there was obtained a portion boiling between 178 and 185° (19 mm): 

 d 20O l,0137, « D -f 52°12\ n D + 1,52822, mol.refr. found 66,81, calc. for C 15 H 24 Or 66,00, 

 calc. for C15H04O/2 67,71. This body, therefore, represents a mixture of bi- and 

 tricyclic vetivenol. The acid of fraction C was identical with vetivenic acid. The 

 fractions A and B also contained a primary bicyclic vetivenol, which may possibly 

 be identical with that from fraction C. These portions likewise contained tricyclic 

 vetivenol. 



Repeated fractionation in vacuo of fraction A, the ultimate fractionation being 

 conducted over sodium, yielded two hydrocarbons: — 



I. B.p. 123 to 130° (16 mm.); d 20 o 0,9355; « D + 2°16'; n D 1,51126; mol. refr. 

 found 65,32; calc. for Ci 5 H 2 4/ = 64,45, calc. for C 15 U^/T 66,15. 



II. B. p. 137 to 140° (16 mm.); d 20 o 0,9321 ; « D — 10° 12'; n D 1,51896; mol. refr. 

 found 66,42 calc. for C i5 H 24 r 64,45, ca!c for Ci 5 H 2 4/^66,15. 



According to the molecular refractions, fi'a'ction I should consist substantially of 

 a tricyclic simply unsaturated hydrocarbon, while fraction II was to be regarded as 



l ) Berl. Berichte 45 (1912), 2347. 



