6i 



cent., distilling between 266-296° C, was a deep indigo-blue oil. The first fraction 

 was again distilled, when most of it came over between 250-252° C. ; this was 

 but little coloured, was insoluble in go per cent, alcohol, had specific gra\'ity 

 0-9266 at 15° C, and the refractive index, at the same temperature was 1-4926. 

 Although evidently consisting largety of a sesquiterpene, yet, owing to the method of 

 preparation, it must necessarih^ have been far from pure. 



When determining the acid value in the ordinarv ^^"a^■ the separated oil 

 formed a cr\-stalline mass after standing for some hours. The crystals were found 

 to be Guaiol, and these had e\-identlv been held in solution by the substances acted 

 upon directly by potash, or, more probably, were in combination ^\'ith them. The 

 oil separated from the saponification determinations after boiling ^^•ith alcoholic 

 potash, also crvstallised readily on standing. These cr3-stals were Guaiol also. 



To isolate the constituents indicated b}- the determinations given above, a 

 larger quantity of the oil was saponified with alcoholic potash b\' boiling ; water 

 was afterwards added in quantit}-, and the separated oil allowed to crystallise. 

 The crystalline cake was then separated, and the solution slowlv evaporated down 

 to remove the alcohol. It was then filtered and rendered acid by sulphuric acid, 

 when a dark-coloured oil, which was acid to litmus, separated in some quantity. 

 This was Avell washed and treated with an aqueous solution of carbonate of soda, 

 when a portion of an acid nature went into solution. The solution was then 

 thoroughlv extracted hv ether, and the ether e^•aporated. The oil thus obtained 

 was but little coloured, was thick and somewhat ^'iscous, and evidently, from 

 the mode of extraction and marked colour reactions, was a phenol. A^'hen placed 

 on ice it did not crvstallise, although it thickened considerabh'. It had most 

 markedly the odour so characteristic of CaUitris timber. When dissoh'ed in 

 alcohol, a solution of ferric chloride gave practically no reaction, ^'\'hen the 

 phenol was dissolved in alcohol -and bromine added, no colour was produced, but 

 after the alcohol had evaporated, the phenol changed to a deep purple colour; 

 this colour was again destroyed by addition of alcohol. WTien dissolved in acetic 

 acid and bromine added, the colour changed to red at once, quickly becoming a 

 rich purple. On standing some time in the air it became an indigo-blue colour^ 

 and the colour was not changed by boiling. This colour reaction is probably due 

 to the formation of a trace of h}'drobromic acid given oft' in the formation of the 

 bromide, because both hydrobromic and hydrochloric acids gave a similar reaction, 

 although slower. The colour was destroyed on the addition of water, a turbid 

 solution being formed by the precipitation of the bromide. \\'hen the phenol was 

 dissolved in strong aqueous alkalis and afterwards acidified with hydrochloric 

 acid, a red colour was also produced. When dissolved in acetic acid and a few 

 drops of sulphiuric acid added, the solution changed immediately to dark red, 

 soon becoming deeper in colour ; e"\'entually the colour became a rich deep purple, 

 which was permanent for some days. When a drop of nitric acid was added with the 



