Essential Oil of Sage. 341 



8. About 20 o-nns. of the terpene boiling at 157° was 

 surrounded by a freezing-mixture, and concentrated sulphuric 

 acid was added drop by drop, the liquid not being allowed to 

 become warm. A trace of sulphur dioxide was evolved, and a 

 deep-red semisolid mass was formed. After 24 hours this 

 was distilled in a current of steam ; the distillate was dried 

 and fractionated ; the greater portion boiled between 175° 

 and 178°, and gave the reactions of cjmene. On analysis, 

 the following numbers were obtained : — 



0-1885 grm. gave 0-6125 grm. CO2, and 0-181 grm. H2O. 



Calculated for C^o 11^,. Found. 



Carbon 89*55 88-61 



Hydrogen 10-45 10-72 



A small quantity of this cymene was oxidized by chromic 

 liquor ; it yielded terephthalic and acetic acids. 



About 7 per cent of cymene was obtained from the 

 terpene. 



9. Twelve grms. of the terpene, placed in a flask sur- 

 rounded with snow and salt, was subjected to the action of 

 bromine, added drop by drop through a narrow tube. The 

 bromine was very rapidly absorbed, a hissing noise being 

 produced on the addition of each drop. When no further 

 absorption appeared to take place, it was found that the liquid 

 weighed 25 grms. In order to convert 12 grms. of Gio H^g 

 into Cio H16 Brg, 14 grms. of bromine (in round numbers) are 

 required ; 13 grms. were used in the foregoing experiment. 

 The liquid thus obtained was a heavy colourless oil. On sub- 

 mitting it to distillation, torrents of hydrobromic acid were 

 evolved, and a nearly colourless liquid came over, which, 

 how*ever, quickly darkened, until of a reddish-brown colour. 

 On attempting to distil this liquid, it was again decomposed, 

 yielding hydrobromic acid, a distillate boiling from 175° to 

 180°, another and heavier portion boiling from 220° to 240°, 

 and a considerable quantity of black resin. This process was 

 repeated several times v/ith the same result ; nevertheless 

 the greater portion of the liquid eventually distilled betvv^een 

 220° and 240°. That fraction which boiled between 1 75° and 

 180° gave all the qualitative reactions for cymene ; on oxi- 

 dation, it yielded terephthalic acid. 



Like the other terpenes of the formula Cio Hig, ih.Q lower- 

 boiling terpene from sage-oil appears to be readily converted 

 into a dibromide, which is decomposed by the action of heat, 

 with the formation of cymene. This decomposition does not. 



