— 148 — 



On reducing phthalide, Semmler observed the primary formation 

 of phthalic alcohol which is not stable towards alcoholic potash. 



He explains the formation of these glycols by the ether-like linking 

 of the oxygen atom with two carbon atoms in one ring. In the first 

 instance an alcohol aldehyde is formed with addition of nascent 

 hydrogen, and from this, by further action of the nascent hydrogen, 

 the glycol. The ring- formation has doubtless some influence on the 

 comparatively good yields. 



Terpineol. With regard to the constitution of the various 

 terpineols and their behaviour towards hydrohalogen acids, see under 

 terpinene (p. 137). 



Terpinenol. See under terpinene (p. 136). 



B o r n e o 1 . In our last Report we made a communication with 

 reference to a work by W. Borsche and W. Lange 1 ) on the pro- 

 duction of thioborneol from pinene hydrochloride. The authors 

 make a somewhat belated reference to a previous work (which they had 

 overlooked at the time) by W. Wuyts 2 ), who had produced thio- 

 borneol by a different method. The same subject has been studied 

 by J. Houben and H. Doescher 3 ) who succeeded in producing 

 hydropinene sulphinic acid, hydropinene carbithio acid, 

 thioborneol, and thiocamphor, and whose results on most points 

 agree with those of the above-mentioned authors. The thioborneol 

 obtained by Houben and Doescher by the action of sulphur on 

 hydropinene magnesium chloride melts at 63 °, and boils at 94 to 95 

 (12,5 mm. pressure). The oily distillation residue consists of hydro- 

 dicamphor, bornyldisulphide, and small quantities of a body still richer 

 in sulphur; when extracted with ether, it yields in the fractional distil- 

 lation in vacuo thioborneol and thiocamphor, — results which pre- 

 viously had also been obtained by Wuyts. Oxidation of thioborneol 

 with chromic acid yielded bornyldisulphide (m. p. 178 ). Although the 

 bornyldisulphide obtained by Borsche and Lange showed the 

 m. p. 121 , a product obtained by Wuyts from camphor again melted 

 at 175 to 1 7 6°. If a sufficiently high temperature is employed, 

 almost the whole quantity of the sulphur-containing products formed 

 from sulphur and hydropinene magnesium chloride is converted in 

 thiocamphor, which, however, oxidises already when simply left 

 standing exposed to air. The thiocamphor obtained by distillation 



*) Berl. Berichte 39 (1906), 2346; Report October 1906, 121. 



2 ) Berl. Berichte 36 (1903), 869. 



3 ) Ibidem 39 (1906), 3503. 



