228 A. R. PENFOLD AND F. R. MORRISON. 
odour resembling safrol. The yield of oil was practically 
constant, 0°4%. The principal constituent was found to be 
a new phenol ether occurring to the extent of 90% for which 
we propose the name “‘Croweacin.’’ It contains one 
methoxy group and in its general characters appears to be 
related to safrol. Its molecular formula is Oi;H;203 and 
so far as we are aware it hag not hitherto been described. 
It is proposed to continue the investigation of this body 
and a paper dealing with its chemistry will be submitted at. | 
a later date. It was thought advisable to put on record 
its isolation, together with a note of its general chemical 
and physical characters at the earliest opportunity. 
An interesting feature worth noting is that although the 
oil is optically inactive, on fractional distillation it is 
resolved into a mixture of the inactive phenol ether with 
both dextro and levo-rotatory bodies, which together 
neutralise one another as regards optical activity. 
Experimental. 
Two lots of leaves and terminal branchlets, totalling 
3515 lbs. collected at Middle Harbour, near Sydney, yielded 
on distillation with steam the following crude oils, possess- 
ing the chemical and physical characters, as shown in table: 

: e Specific : Refractive 
Date we ht of Nee Gravity Bi Index 
SONS 15/15°°C. 202°0; 


14/3/1922 1183ibs.| 0:4% 1:124 | inactive | 1:5321 
29/8/1922 233 Ibs. 04% 1-109 ditto 1:5302 



Solubility in 80% | Ester No. hot | Ester No. 1} hours ; 
alcohol by weight 13 hours after acetylation | Percentage Methaxyt 
5:5 vols. 75 | 75 13°73 (=about 90% 
| C,,H,293) 
5:5 vols. D0 S68 13°87 ditto 



On distillation at 10 mm. the first lot of oil yielded 1% 
boiling below 128° O., and 98% between 128-133° O., 
whereas the second consignment gave 1% distilling below 
65° O., 55% between 65—129° C., 82% at 129—132° O., and 
10% between 132—140° CO. 
