232 A. R. PENFOLD AND F. R. MORRISON, 
The oxidation liquor after removal of the neutral body 
Was evaporated to a smaller bulk, but only traces of acid 
‘bodies separated on addition of dilute sulphuric acid. 
(b) On treating 10c.c. ofthe ether with 30grams powdered 
potassium permanganate, 4 grams potassium hydroxide, 
700 c.c. water and 700 grams ice in a similar manner, besides 
the neutral body, several grams of a solid acid were sepa- 
rated. It crystallised from alcohol in brownish tinted 
rosettes and melted at 153° C. 
On combustion it gave the following results :-— 
(1) 0°1002 gm. gave 0°2016 gm. CO, and 0°0396.gm. H,O 
O - 54°87, H —4°39% 
(2) 0°1060 gm. gave 0°2130 gm. CO. and 0°0415 gm. H,O 
— O—54°80%, H—4°34% 
O,H.O; requires C=55°107, H=4°08%. 
Titration of 0°1944 gram in absolute alcohol with deci- 
normal solution sodium hydroxide required 9°8c.c. M.Wt. 
=198. Theory requires 196. : 
The foregoing evidence points to the phenol ether 
possessing an allyl or propeny! side chain similar to other 
bodies like safrol, elemicin, etc., as an acid of this formula 
could only result from the ‘splitting off’ of such a chain 
from an ether of molecular formula OyHi203. As stated 
above, further work is being carried out and will be ge: 
lished as a Part IT contribution. 
Minor constituents.—A dextro-rotatory sesquiterpene 
was detected in the fractions boiling a little higher than 
the ether by the colour reactions which it gave with bromine 
vapour and sulphuric acid in acetic anhydride solution, 
which were identical with those given by similar constitu- 
ents from other Australian essential oils. A paraffin of 
melting point 64—65° C. was also isolated from the high 
boiling residues. 
This essential oil consists, therefore, of the phenol ether 
(907%), together with d-«-pinene, sesquiterpene, a paraffin, 
and an unidentified levo-rotatory body. 
