62 



sulphuric acid the changes through red to phuu colour were more rapid, but eventu- 

 ally the same result was obtained. To a portion of the original phenol placed 

 on a watch-glass, a drop of sulphuric acid was added, a red colour was produced, 

 eventually becoming purjile on the edges as with the acetic acid solution. When 

 a little of the phenol was dissolved in acetic acid on a watch glass, and the vapour 

 of bromine passed over it, a purplish colour instantly formed, soon becoming 

 a rich purple. This reaction is ^•ery delicate, and by its aid it is possible to deter- 

 mine the presence of the phenol in Callitris timber, the shavings being treated 

 with ether-alcohol, and the solution evaporated to dryness before dissolving in 

 the acetic acid. The difference in odour, in consistency, reactions with ferric 

 chloride, together with its other marked colour reactions, show this phenol to 

 be distinct from carvacrol. The marked colour reactions point to the origin of 

 the indigo-blue oil obtained when redistilling the crude product. 



When the original thick crude oil was agitated with a lo per cent, solution 

 of aqueous soda, a semi-solid mass was at once produced. After some time 

 water was added and the mixture agitated, but the bulk of the oil still remained 

 as a pasty mass, and this was filtered off and washed. It was readily soluble in 

 ether, and on evaporating the ether a thick oil remained which soon crystallised, 

 and from which Guaiol was obtained. When the alkaline filtrate was treated with 

 a large quantity of water, it was partly decomposed, a small quantity of oil 

 separating. 



After standing some time with repeated agitation, the aqueous liquid was 

 filtered and thoroughly extracted with ether. On evaporating the ether the 

 phenol was obtained. This gave all the reactions, and had the characteristic 

 odour of the phenol as obtained previously by saponification. The phenol is 

 readily soluble in acetic acid, in ether, alcohol, chloroform, and in the usual 

 organic solvents. 



If on further investigation this phenol is found to be new, as appears to be 

 the case, then the name Callitrol is proposed for it. 



The oily distillate ivom the timber of C. Macleayana, from which the Guaiol 

 had been removed, was of a deep red colour ; it was slightly more aromatic than 

 the oil from C. glauca. It was soluble in an equal volume of (So per cent, alcohol, 

 and remained clear with excess. It was soluble in two volumes 70 per cent, 

 alcohol, but became turbid with five volumes. The saponification number of the 

 esters was 22-34, while the acid value was 7-4. The phenol was extracted in the 

 manner previously described, and although somewhat small in amount, yet it 

 was identical with that obtained from the limber of C. glauca. (iuaiol was also 

 obtained from the product of saponification as willi llie latter species. 



The characteristic colour reaction forCalHtrol conld nol he obtained from the 

 timber of Widdringtonia from South Africa; so e\id(iifl\- llial phenol is absent. 



