Essential OH of Boronia pinnata. 17 



The product was dark coloured, and had a strong phenolic 

 odour. It ■^\-as dissolved in ether, and the acid removed from the 

 phenol by shaking with a solution of Sodium carbonate. The- 

 small quantity of acid when finally purified, was crystalline, and 

 melted at ISO-IGCC. It was not cinnamic acid, and perhaps con- 

 sisted of trimethylgallic acid, which is formed by oxidation of 

 elemicin. 



The ether solution of the phenol after removal of the acid was 

 evaporated to dryness. The residue had a strong phenolic or 

 creosote-like odour, was not crystalline, and when dissolved in 

 alcohol gave a purplish-brown colour with ferric chloride, which 

 colour remained persistent. 



Tests for some of the well-known phenols gave negative results, 

 and as the amount was small, its identity could not be determined. 



The oil, after the removal of the phenol and free acid, was re- 

 peatedly shaken for some days, with a saturated solution of sodium 

 bisulphite, but no combination took place. Aldehydes were thus 

 absent. 



Distillation of the Crude Oil. 



100 c.c of the crude oil were submitted to distillation under 

 atmospheric pressure. A few drops of an acid water with a little- 

 oil came over below 160°C. (uncorrected). Between 160-250° 

 only 16.5 c.c. came over as first fraction, 10 c.c. of which distilled 

 below 180°. 



Thes temperature rose rapidly to 259", and distillation then pro- 

 ceeded as follows : — ■ 



259-265° = 18 c.c. 

 265-270° =50 c.c. 

 270-274° = 63 c.c. 

 274-280° = 70 c.c. 

 This fraction was then separated, and although 3 c.c. of an oil 

 came over on continued heating, yet the temperature did not rise- 

 beyond 280°. The residue in the still was a dark hard pitch-like- 

 substance, which powdered readily when cold. 

 71)6 first fractio7i gave the following results : — 

 Specific gravity at 15°C. =0.8657. 

 Rotation aD= +15.9°. 

 Refractive index at 20° = 1.4639. 

 Cineol was not present. The oil of this fraction was fluorescent. 

 15 c.c. of the first fraction were again distilled, when 7.5 c.c. 

 came over below 158°C., and 5.5 c.c. between 158-190°. The 



3 



