Schorger—Chemistry of American Conifers. 749 
tine oil of this species. Bromination of portions of the oil col¬ 
lected between 170-180° did not yield a solid dipentene tetra- 
bromide, owing possibly to the large amount of phellandrene 
present; however, dipentene dihydrochloride melting at 49° was 
obtained. 
Oxidation of the alcohols obtained by saponification of the 
ester fractions gave a small amount of an oil having a strong 
odor of camphor. The oxidation liquors contained anisic acid, 
m. p. 183-184°. As in the case of the leaf and twig oil of digger 
pine anisic acid indicates the probable presence of methyl chav- 
icol. The fraction boiling between 265 and 284° and having the 
rotation a D2 i°+14.69 was rich in cadinene. The cadinene dihy¬ 
drochloride obtained melted at 117-118° and had the specific 
rotation [a] d -45.66° It may be mentioned that all the cadinene 
fractions from the various oils examined were d-rotatory while the 
cadinene dihydrochlorides obtained were always 1-rotatory. 
The oil has the following composition: furfural, trace; 1-a-pi- 
nene 3%; 1-/Lpinene 49-50%; 1-phellandrene and dipentene 
19%; ester as bornyl acetate 2.0% ; free alcohol as 1-borneol 
7.5%; methyl chavicol (?) ; cadinene 7%. 
The Leaf and Twig Oil of Bed Fir (Abies magnified Murr.) 1 
The properties of the oil were the following: d 15 ° 0.8665; 
n D i 5 ° 1.4861; a D 2o°-16.70 0 acid No. 0.75; ester No. 9.93; ester 
No. after acetylation 36.22; yield of oil 0.154%. 
The oil did not begin to distill until a temperature of 167° 
was reached. By repeated fractionation 3.6 grams of oil were 
obtained distilling between 160-164°. On treatment with ethyl 
nitrite and hydrochloric acid, the intense green coloration char¬ 
acteristic of the formation of pinene nitrosochloride was obtained 
but none of the solid derivative separated out. Oxidation of the 
oil distilling between 164-168° gave nopinic acid melting at 
126-127°; this proves the presence of /Lpinene. Phellandrene 
was the only additional terpene that could be detected. Large 
amounts of phellandrene nitrite melting at 102-103° were ob¬ 
tained. Dipentene could not be detected as either the tetra- 
bromide or dihydrochloride. 
The oil obtained by saponifying the ester fractions gave on 
oxidation so small an amount of solid camphor that it could not 
1 Jour. Ind. Eng\ Chem. 7 (1915) 24. 
