193 
acid, cadinene hydrochloride, as described by Wallach! (melting point 
117° to 118°), separates. 
0.1878 gram substance gave 0.1920 gram AgCl. 
Required for C,;H,,, 2 HCl Found 
Per cent. Per cent. 
Ci. 25.6 25.3 
The hydrobromide was also prepared and recrystallized from ligroin. Its melt- 
ing point (118° to 125°) corresponds to that obtained by Wallach. 
On saturating a solution of one part of the distillate in four parts of 
glacial acetic acid with hydrochloric acid gas at 5°, the hydrochloride 
soon separated in considerable quantity. The solution was kept saturated 
for several hours and then allowed to stand for a day. It was then cooled, 
filtered quickly with suction, and washed with alcohol. ‘Twenty grams of 
the hydrochloride were obtained from 45 grams of the oil. To convert 
the hydrochloride into cadinene it was heated with excess of aniline at 
150°; aniline and aniline hydrochloride were removed with dilute acid 
and the remaining product was distilled with steam and redistilled under 
diminished pressure. It boiled at 164° to 165° (38 millimeters). Not 
enough of the substance was at hand for a determination of its specific 
gravity. Rotation, —39° (5 centimeters, 30°). It will be noted that the 
treatment with hydrochloric acid gas only partially converted the oil into 
cadinene hydrochloride, but a separate determination of the total amount 
of hydrochloric acid which the oil takes up under the conditions of the 
above experiment demonstrated that if it be considered as composed of 
sesquiterpenes, then, for every molecule of the latter it contained two of 
the gas. 
It is evident that cadinene constitutes a large portion of the distillate 
from Oil of Supa. As to the remaining constituents nothing definite 
can be said, for no other crystalline derivatives could be obtained from 
the oil, although many attempts were made. One experiment in this 
direction was especially interesting because it resulted in the conversion 
of the oil into a constant-boiling product. 
Twenty grams of the distillate were added to 100 cubic centimeters of alcohol 
and 5 cubic centimeters of dilute sulphuric acid (1 to 5) and heated for seven 
hours on a water bath with reflux condenser. Afterwards the alcohol was almost 
entirely distilled and the residue thoroughly shaken with water, after which it 
was dried and distilled under reduced pressure. The distillate passed over within 
5°, leaving a small amount of a tarry residue. On redistillation the product 
passed over completely at 161° to 163° (37 millimeters). At 760 millimeters it 
boiled from 271° to 274°. (Cadinene of Wallach, 274° to 275°.) Rotation, 
+10.2° (10 centimeters, 30°). Specific gravity, (Sys) =0-9176. The oil possesses 
° 
a slight odor which resembles that of cadinene but which is quite distinct from 
that of the original Oil of Supa. To judge from the boiling point, it would 
appear to be almost pure cadinene; however, it is dextro-rotatory, whereas the 
‘Ann, d. Chemie (Liebig) (1887), 238, 80. 
