P - 153 — 



Z-thujyl alcohol gave [«] D20 o — 9,12° and was solid at ordinary temperature: 

 m. p. 28°. The liquid d-thujyl alcohol forms a xanthate which splits 

 up at 138°; the xanthate of the solid Hhujyl alcohol is more stable: 

 decomp. pt. 183°. The xanthate of d-thujyl alcohol yields a hydro- 

 carbon possessing the following constants: b. p. 151 ° (759 mm.), d^ 0,8301, 

 n D20 o 1,45150. Most probably this body represents pure «-thujene. The 

 decomposition of Mhujylxanthate leads in all probability to A-thujene 

 (b. p. 147° at 739 mm.). 



Guajol. In order to discover a solution of the question how many 

 ring-systems and double-bonds occur in guajol, F. W. Semmler and 

 E. W. Mayer 1 ) calculated the molecular refraction of the alcohol in question 

 from its sp. gr. and its index of refraction, and calculated both the refractive 

 index and the specific gravity for a temperature of 20°. The values as- 

 certained for guajol as well as for several other sesquiterpene alcohols 

 are set forth in table-form below. It follows from these that guajol is a 

 bicyclic alcohol with a double bond. For purposes of identification it is 

 oxidised with potassium permanganate in aqueous acetone, giving rise to 

 a glycerol Ci 5 H 2 80 3 , m. p. 210 to 211°, which body is possibly the first 

 glycerol of the sesquiterpene series. Ozonisation in glacial acetic acid 

 solution yielded a neutral decomposition product, [b. p. 138 to 144° (7mm.) 

 d 20 o 0,9972; « D 2oo + 96°; n D 1,5276], possibly an oxide. Besides this, there 

 was formed a body C15H24O3, apparently a keto lactone: b. p. 200 to 208° 

 (8 mm.), d 20 o 1,067, n D20O 1,5005. 



J D20O 



Mol.-Refr. 

 found calc. 



Guajol 



Ledum camphor . . . 



Eudesmol 



Solid Cedrol 



Patchouly alcohol . . 

 Caryophyllene hydrate 



i lQQO 

 *20O 



100 o 



20O 

 810 

 20O 



90 O 

 20O 

 ISO 

 20O 

 100O 

 20 O 



0,9074 

 0,9094 

 0,9209 

 0,9496 

 0,9924 

 0,9376 



0,9714 

 0,9814 

 0,9884 

 1,0056 

 1,0284 

 1,0016 



n D100O 

 n D110O 

 nD80O 

 n D9oo 



n D650 



n Dlooo 



1,4716 

 1,4667 

 1,4830 

 1,4824 

 1,5029 

 1,4755 



1,5100 

 1,5072 

 1,5164 

 1,5139 

 1,5245 

 1,5155 



68,35 

 67,35 

 67,99 

 66,46 

 66,19 

 66,90 



/ = 68,07) 

 /=6,078j! 



/= 68,07)*' 

 66,36L 

 66,36 f 

 66,36)" 



sec.-Phenylethyl alcohol. B. Holmberg 2 ) describes the previously 

 unknown optically active methylphenylcarbinoles (secondary phenylethyl- 

 alcohols). He started from the active phenyl ethylamines which, in dilute 

 sulphuric acid solution, he treated under strong cooling with nitrous acid. 

 Z-Phenylethylamine gave rise to d-phenylethyl nitrite and to sec. <#-phenyl- 



!) Berl. Berichte 45 (1912), 1390. 

 2 ) Berl. Berichte 45 (1912), 997. 



