— 127 — 



ordinary pressure apparently a little below 215 , water being given off. 

 In the course of this reaction, phellandrene was formed, and determ- 

 ined by its odour and by the nitrite-reaction. It follows from this, 

 that a displacement of the double linking must have occurred in 

 some phase or another possibly at as early a stage as in the Grignard 

 reaction. But the fact that the synthetically prepared alcohol con- 

 tained a high proportion of terpinenol- 1 could be proved by oxidation to 

 1, 3, 4-trihydroxyterpane, m. p. 120 to 121 . This latter substance, when 

 treated with hydrochloric acid, yielded, in addition to cymene, a ketone 

 which was doubtless identical with A 1 -menthenone. We may further 

 place on record the fact that the optical rotatory power of sabinene 

 hydrate in 1 9,1 7 °/ ethereal solution is [«] D -(-53,67°, while that of 

 synthetic terpinenol-4 is [«]p -f- 10,53°. 



Guajol. A. Gandurin 1 ), in a preliminary communication, describes 

 experiments relating to the sesquiterpene alcohol guajol. For the pur- 

 pose of isolating the compound, guajacum-wood oil was shaken up with 

 ether for 12 hours, the resultant pulpy mass filtered with the suction 

 pump, again shaken with ether and recrystallised from alcohol. The 

 guajol (C 15 H 25 OH) obtained by this process occurs in prismatic crys- 

 tals; it melted at 91° and, in alcoholic solution, had the rotation 

 Wr>25° — 25,64°. When the substance was rubbed in the dark with 

 a glass-rod, a pronounced irridescence of a blueish colour ensued. A 

 hydroxyl determination according to Tschugaeff-Zerewitinoff 

 showed the alcohol to be monatomic, the determination of the rate of 

 esterification disclosed its tertiary character. Dihydro-guajene (C 15 H 26 ) 

 prepared according to Semmler's process by heating with zinc-dust, 

 showed the following constants: b. p. 122° at 11 mm. press., d^ 0,9089, 



25° 



d-^o 0,8914, n D20 5 2° 1,49317, Mdi8,5° — 26,65° molecular refraction 

 determined: 66,99, calculated for a bi-cyclic hydrocarbon C 15 H 26 / = 66,5 5. 

 As, according to Semmler, secondary alcohols are not attacked by 

 zinc- dust, the formation of dihydro-guajene also points to the tertiary 

 character of guajol. For the ether C 15 H 25 OCH 3 , obtained by the 

 action of methyl iodide upon the potassium compound, the following 

 properties were established: b. p. 141 to 143° at 9 mm. press., 



no 25° 



d 4o 0,9513, d^ 0,9332, n D185 o 1,48963, [«]d20° — ii^i mol. refr. 

 found 72,77, calculated for a bi-cyclic ether C 15 H 25 OC £13/^72,83. 

 Application on Tschugaeff's xanthogenate method showed that — 

 corresponding to the behaviour of tertiary alcohols — it was impossible 

 to isolate the methyl guajyl - xanthogenate, because it decomposed 

 immediately into guajene. This hydrocarbon showed the follow- 



*) Berl. Berichte 41 (1908), 4359. 



