294 H. G. SMITH. 



Oxidation of the aldehyde with potassium permanganate. — The 

 aldehyde was readily and energetically attacked by an alkaline 

 solution of potassium permanganate. The odour of the original 

 aldehyde soon changed to one indicating somewhat that of 

 cinnamon. This odour soon vanished and was eventually replaced 

 by the characteristic odour of pure eucalyptol. The excess of per- 

 manganate was reduced, the clear filtrate acidified with hyrdochloric 

 acid and evaporated down to a small bulk; a white solid acid was 

 thus obtained, this was filtered off, well washed, and purified from 

 a boiling mixture of two parts alcohol and one part water ; on 

 boiling off the alcohol most of the acid precipitated, it being not 

 readily soluble in boiling water. It was easily soluble in alcohol 

 and in ether. This acid melted at 259 — 260° C. with formation 

 of the anhydride. The acid readily sublimed on melting, forming 

 a well crystallised sublimate which melted at 152° C. Both the 

 acid and the anhydride are crystallised bodies before and also after 

 melting. The anhydride readily sublimed, it being easily driven 

 from one watch glass to another ; it dissolved easily in a small 

 quantity of boiling water, and crystallised out beautifully on 

 cooling, it being practically insoluble in cold water ; it was very 

 soluble in alcohol and in ether. The original acid was apparently 

 not regenerated by boiling the anhydride in water, as the separated 

 crystals melted again at the same temperature as the sublimate. 

 The anhydride commenced to sublime at about 135° C, but if the 

 heating was somewhat rapid it melted sharply at 152° C. 



From the characters of the acid and its anhydride, formed by 

 the oxidation of the aldehyde with potassium permanganate, and 

 the formation at the same time of eucalyptol, it might be considered 

 that the products were cineolic acid and its corresponding 

 anhydride; but the melting points obtained do not agree with 

 those given for cineolic acid ana its anhydride, consequently 

 further investigation of these oxidation products is required. 



The name proposed for this aldehyde is aromadendral, utilising 

 the name for the genus given by Dr. W. Anderson, the surgeon 

 of Captain Cook's second and third expeditions. The correspond- 



