248 
E. M. Watson. 
EXPERIMENTAL. 
The oil distilled completely in three hours and the undried oil had the 
following pljysical properties at 20° (.!. : — Specific gravity, 0-923 ; refractive 
index, 1-406: specific rotation, -0-22°. Tt ^cas soluble in two volumes of 70 
per cent, alcohol. Its acid A-aluc was 0-6 : its saponification values Avere : — 
Cold, 1-9 ; hot, 3-2, corresponding respectively to 0-07 per cent, of geran^ 1 
acetate and 1 ■ 1 per cent, of total esters calculated as 012 ^ 20 ^ 2 - saponifi- 
cation values of the acetylat.ed oil \Aere : — Cold, 43-8 ; hot, 52-5, correspond- 
ing respectiA^ely to l]-r> per ceTit. of alcohols calciilated as geraniol and 13-5 
per cent, of total alcohols calculated as CioHigO. The aldehyde content of 
the oil A\as 0-12 millimole per giam of oil, ec|iuA'alent to 1-8 ])er cent, of 
aldehydes calciilated as CJ 0 H 14 O. Tlio cineole content of the dried oil was 
70-9 per cent. The usual colour reaetious for aromadendrene Avere obtained 
but the oil gave no reactions for ])inene or pliellandrene. 
The oil Avas redistilled and tlie follow ing fractions Avere separated : — 
Fraction. 
Boiling 
Amount 
Specific 
Re tract iA’e 
Specific 
Range. 
per cent. 
GraA’ity. 
Index. 
Rotation. 
1 
tqi to 160° 
2-8 
0-897 
1-442 
714-1° 
2 
16C°— 167° 
11-75 
0-901 
1-462 
+ 16-1° 
3 
167°—-169° 
11 -25 
0-912 
1-461 
+ 6-5° 
4 
169°— 176° 
57-4 
0-920 
1-461 
1-2° 
The 
folloAAing 
residue was further 
fractions separated 
fi’actionated 
under 
reduced pressure 
and til 
5 
80°— 90° /27 mmy. 
2-2 
0-959 
1-480 
—23-8° 
6 
90°— 110°/26mms. 
6-0 
0-967 
1-494 
—36-2° 
7 
110°— 120°/25 mms. 
1-7 
0-965 
1-496 
—19-7° 
As the initial boiling commenced, the formation of A\ hite insoluble material 
w^as noted and from the final residue 2-3 per cent, of AA'hite amorphous solid 
AA^as separated by addition of ether, folloAAed by filtration. 
Fraction 1 contained some Avater which was separated. This contained 
both aldehydes and free acids, the latter including butyric, probably A^aleric, 
and either or both formic and acetic acids. From this aqueous portion a 
small quantity of colourless crystals se]iarated. These crystals are neutral, 
soluble in alcohol, may be recrystallised from Avater, give no colour Avith 
ferric chloride, and melt at 145°. From the oily part of this fraction no re- 
actions for pineno were obtained. 
I'raction 2 contained 59-3 per cent, of cineole, A\ as colourless and pleasant- 
smelling, and bad cold and hot saponification A'alucs of 5-9 and 8-2 rcspect- 
iA^eJy. 
Fraction 3 was similar and contained 76-5 pei’ cent, of cineole, Avhilst 
Fraction 4 contained no less than 88-8 per cent, of cineole. The saponifica- 
tion values of these two fractions were respectively 2-2 and 2-9 (cold) and 3- 1 
and 3-6 (liot). No crystalline nitrosito aars obtained from Fractions 2, 3, 
and 4. 
I’raction 5 was colourless and contained the greater part of tlie esters, 
haAnng cold and hot saponification A’alues of 56-6 and 63-9 respectively, 
corresponding to 20-8 and 22*4 per cent, of esters, calculated as Ci 2 R 20 ^ 2 - 
This fraction, as well as fractions 6 and 7, contained a small amount of 
aldehyde. 
Fractions 6 and 7 had cold saponification valaes of 19- 1 and 15-8 respect- 
ively and hot saponification values of 22-5 and 20-3. 
