736 Wisconsin Academy of Sciences, Arts, and Letters. 
caprinate, C 9 H 19 COO Ag, calculated 38.66%—found 38.45%; 
Ag in silver acetate, CH s COO Ag—calculated 64.64%—found 
64.42%. Acetic, caproic and formic acids were also found free, 
in the old oil. 
The rectified oil had approximately the following composi¬ 
tion: d-a-pinene 60-61%; dipentene 6-7%; free d-borneol 
11 %; bornyl acetate 11.5% ; cadinene 6-7%; losses 5%. 
Leaf Oil of Douglas Fir (Pseudotsuga taxifolia Britt ) 1 
The oil of this species was examined by Brandel and Sweet 2 
who claimed to have found free borneol, bornyl acetate and con¬ 
siderable camphene; pinene and limonene were thought to be 
present but were not identified. The results obtaind by the 
author were very different. Camphene could not be detected 
and / 2 -pinene was found to be the principal constituent. 
A series of six samples were examined with the following re¬ 
sults: d 15 ° 0.8727-0.8759; n Dl5 ° 1.4758-1.4780; a D20 o -17.02 o to 
-22.17; acid No. 0.65-1.10; ester No. 11.13-24.25; ester No. after 
acetylation 27.50-51.78. 
Furfural was detected in the first fraction of the oil by the 
deep rose-color obtained on treating the aqueous extract with 
aniline-hydrochloric acid solution. From a fraction b.p. 156- 
157°, d 15 ° 0.8682, a D 22 0 -ll- 94 0 , a-pinene, m. p. of nitrosochloride 
103°, was obtained; its nitrolpiperidine melted at 118°. Examin¬ 
ation of the fraction b. p. 160-162° for camphene gave negative 
results. 
A fraction b. p. 170-172°, d 15 o 0.8628, a D 2 5 o- 28 . 12 0 gave a 
dihydrochloride m. p. 50°. The next fraction b. p. 172-178.2°, 
d 15 ° 0.8616, a D 2 5 -26.24 0 , gave with difficulty a tetrabromide m. 
p. 117-119° after two crystallizations from ethyl acetate, and 
after a third crystallization, at 121-2°. The high rotation of the 
fractions combined with the melting point of the tetrabromide 
indicate the presence of liminene in addition to dipentene. 
Borneol was isolated from a fraction b. p. 208-213, a D 2 6 0 - 
19.42°, as the pthalic ester. The liberated alcohol on oxidation 
gave camphor melting at 174°. The borneol was in part com¬ 
bined with acetic acid since the silver content of the salt isolated 
1 Jour. Am. Chem. Soc. 35, 1895 (1913). 
2 Pharm. Rev. 26, 326 (1908). 
