374 R. T. BAKER AND HENRY G. SMITH. 



(d) If the vapours of bromine are allowed to fall down a 

 test tube on to a solution of two drops in glacial 

 acetic acid, a violet colour at once forms, changing 

 to indigo-blue on standing. 



This sesquiterpene appears to be present in the high 

 boiling portions of the oils of many species of Melaleuca, 

 and the above colour reactions are readily obtained with 

 them. 



The amount of cineol in the crude oil is but small, it 

 was determined by the resorcinol method in the first 

 fraction, and calculated for the crude oil. The whole of 

 the cineol was removed from the first fraction by the aid 

 of 50 per cent, resorcinol, and the separated terpenes again 

 rectified. Nothing distilled below 175° 0. (corr.), so that 

 pinene cannot be present but in traces. The greater por- 

 tion of the terpenes distilled between 175 - 178° 0., and 

 gave other indications for limonene or dipentene. 



The ester in this oil is probably terpinyl-acetate, as the 

 acid was determined as acetic, and the odour of the 

 separated oil, after saponification, reminded strongly of 

 terpineol. Free terpineol is probably also present, as on 

 boiling the oil with acetic anhydride and anhydrous sodium 

 acetate in the usual way, over 5 per cent, of an alcohol 

 was shown to be present. 



The high boiling fraction when agitated with acetic 

 anhydride did not easily dissolve, so that it was possible to 

 remove largely the ester and the free alcohol from the 

 sesquiterpene by the method of agitation. 



Experimental.— The material was collected at Gosford, 

 in this State, and distilled in January, 1911. 208 flbs. of 

 material (leaves and terminal branchlets) gave 10 ounces 

 of oil, equal to 0*3 per cent. The crude oil was of a dark 

 amber colour, somewhat viscous and greasy in appearance 

 — similar in this respect to the oil of M. bracteata — and 



