86 
PROCEEDINGS OF THE ROYAL SOCIETY OF QUEENSLAND. 
The remainder of the oil was fractionated several times to give three 
head fractions. The first of these had the following constants : — 
B.P. 
. . 
. . 
• • 
. . 54 °C. @ 4 mm. 
^155 
. . 
• • 
• • 
•8607 
n— 
D 
. . 
• • 
• • 
1-4880 
[-Id 
• • 
• • 
• • 
0 
This was identified as p-cymene by oxidation to p-toluic acid as 
follows : — Two mis. of the fractions were refluxed with 20 nils, of dilute 
HN0 3 (1 HNOo : 3 H 2 0) for several hours. O 11 standing overnight 
crystals of p-toluic acid separated out. These were recrystallised from 
w>ater and melted at 176-177° C. undepressed 011 admixture with a 
sample of p-toluic acid. 
The next head fraction had — 
d 15 . 5 • . . . . . . . *9216 
nf 1-4812 
[a.]^ . . . . . . . . -f- 20 
This contained an ester as indicated by ester number determinations 
on the fraction. Two mis. of this were hydrolysed with alcoholic KOH 
and the presence of acetic acid in the alkaline solution determined by 
qualitative tests. The impure alcohol was isolated in the usual way and 
was found to have the characteristic odour of terpineol. This was 
confirmed by conversion into its acid phthalate, M.P. 116°, by the method 
used by Kenyon ( 1 ) . 
The last fraction consisted of sesquiterpene and sesquiterpene 
alcohol giving the characteristic violet colour on treatment with bromine 
vapour in the presence of acetic acid. Only a few mis. of this fraction 
were available and it was not further investigated. 
Summary . — The essential oil of Ilalfordia Keudach has been shown 
to consist of d-a-pinenc (90 per cent.), cymene (4 per cent.), terpineol 
acetate, sesquiterpene and sesquiterpene alcohol. 
REFERENCE. 
(1) Kenyon, J. C. S. (1924), 125, 2504. 
