EUCALYPTUS OIL CONTAINING GERANYL ACETATE. 145 



great. Some free alcohol was found to be present in the oil of 

 E. macarthuri, most probably geraniol. 



The oil separated after saponification is readily oxidised to citral, 

 using potassium bichromate. The pure aldehyde was obtained by 

 agitating the oxidised product with sodium bisulphite, separating 

 the crystals formed, purifying and decomposing them in the usual 

 way. The tests applied, together with the odour, showed the 

 product to be citral. 



Pure geraniol was obtained by treating the saponified oil with 

 dry calcium chloride, removing the unacted upon oil with benzene, 

 allowing the benzene to evaporate, and decomposing the compound 

 with water; the washed oil was then steam distilled. The product 

 was a colourless oil of a fine rose odour, it boiled at 224 - 225° C. 

 (uncor.), and had a specific gravity 0*885 at 20° C. 



On distilling the oil under atmospheric pressure only a few drops 

 came over below 172° C., 1 between 172 and 219° C. 10 per cent, 

 distilled; between 219 and 229° C, 63 per cent, was obtained;, 

 the thermometer then rapidly rose to 266° C, between 266 and 

 282° C, 16 per cent, came over. Some decomposition of the ester 

 had taken place under atmospheric pressure, the odour of acetic- 

 acid being detected. The first fraction contained neither eucalyptol 

 nor phellandrene, but a green coloration being obtained with the 

 sodium nitrite, indicated that a small quantity of pinene was 

 present. The second fraction contained most of the geraniol. 

 The third fraction consisted largely of eudesmol, the oil crystallising 

 to a solid mass in the bottle soon after distilling. 



The optical rotation of the crude oil after removal of the free 

 acid was + 3-6° in a 100 mm. tube, and the fraction 219 - 229° C. 

 had a rotation in the same tube of +1'0°. The specific gravity 

 of the crude oil at 15° C. was 0-9245, this comparatively high 

 specific gravity was due to the presence of the stearoptene. The 

 specific gravity of the fraction 172 - 219° 0. was 0-8823; of the 

 fraction 219 - 229° C. 0-9111; while that of the fraction 266 - 



1 Temperatures corrected to the nearest whole degree. 



J— Nov. 7, 1900. 



