I 



u 



3Q 6 



contains small amounts of acetic and butyric acids, was washed with dilute 

 sodium bicarbonate, extracted with ether, the ether removed, and the phenols 

 distilled. 



The product from the oil of E. linearis was utilised for the earlier 

 determination of tasmanol, whilst that for the later investigation was obtained 

 from the oil of E. Risdoni. 



For the work on australol the oil of E. hemiphloia was utilised. 



TASMANOL. 



This is a liquid phenol, but little coloured when prepared in as pure 

 a condition as was possible, but it darkened somewhat on keeping. The product 

 from E. linearis had specific gravity at 23 ° C. = 1-077; refractive index at 22° = 

 1-5269, and was optically inactive. Its boiling-] oint under atmospheric pressure 

 was 268-273° C. (uncorr.), and at 175 C. under 25 mm. pressure. It contained 

 one methoxv group. The phenol was soluble in ammonia, partlv so in sodium 

 carbonate, but not in bicarbonate. It dissolved slightlv in boiling water. 



The tasmanol from E. Risdoni had specific gravitv at 20° C. = 1-0809; 

 refractive index at 20° = 1-5241, and was optically inactive. Its boiling point 

 was 164° C. at 12 millimetres pressure. The phthalein fusion gave a light 

 orange colour similar to that for australol, but of no distinctive value. 



The reaction with ferric chloride in alcoholic solution is characteristic, and 

 the deep blood-red colour which is at first formed remains persistent for davs after 

 the alcohol has evaporated, even becoming more crimson on standing. 



The odour reminds one somewhat of carvacrol under certain conditions, but 

 is more aromatic. 



AUSTRALOL. 



This crystallised phenol could be best prepared from the oils of the tvpical 

 " Boxes," such as E. hemiphloia, E. Woollsiana, &c. We utilised the former 

 of these species beca.use it grows plentifullv in the immediate neighbourhood 

 of Sydney. 



The phenolic bodies were first prepared in the manner described above, 

 and afterwards distilled under reduced pressure. As australol boils at a consider- 

 ably lower temperature than tasmanol it was not difficult to obtain the phenol 

 fairly pure by fractionation under reduced pressure. 



Australol boils at 115-116° C. under 10 millimetres pressure, and shows a 

 tendency to remain for a long time in the liquid condition ; if, however, the minutest 

 particle of crystal is added, the whole mass instantly solidifies. 



The specific gravity at 20° C. was 0-9971 ; refractive index at the same 

 temperature = 1-5195, and was optically inactive. The phenol was best purified 

 from solution in xylene, as it crystallised well from that solvent. It remained 

 more or less as a varnish when dissolved in alcohol, chloroform, acetone and the 

 usual organic solvents. The long thin prism crystals (enlarged 45 diameters), as 

 crystallised from xylene, are well shown in the accompanying photograph. 

 Thev exhibit the peculiarity of rounded ends to the prisms. 



The phenol sublimes splendidly, and is unaltered by this treatment ; it 

 was thus possible to obtain it quite pure. It was soluble in ammonia, but not in 

 sodium carbonate or bicarbonate. 



Australol melts at 62° C, and has a tendency to remain in the super-fused 

 condition for some time if not seeded. It forms a benzoyl compound which melts 

 at 72-73°, when crystallised from petroleum ether. 



In alcoholic solution ferric chloride gives a fleeting greenish vellow colour 

 at first, quickly changing to bright yellow. The phthalein fusion gives an 



