present; after the solution became clear the unabsorbed 

 oil amounted to 21-22 per .cent of the whole. This 

 oil had the same properties as the pinene above which 

 had been purified by distillation. 



CINEOL The remainder of the oil from the first 

 fractions was added to fractions 5 and 6, and redistilled; 

 after several fractionations a fraction was obtained 

 which boiled at 176. A comparison of the constants 

 of this fraction with those of pure cineol shows that 

 this fraction was cineol. 



Distillate PURE 



176-177 CINEOL 



Boiling point 176-177 176 



D20 0.930 0.9267 



N^ 1.457 1.4559 



Melting point iodol (after recrystallization) . . 111 112 



The iodol formed from this distillate after recrystal- 

 lization melted at m. Cineol iodol melts at 112. 

 A quantitative analysis by the U. S. P. phosphoric 

 acid method gave 47 per cent cineol by volume. 



EUDESMOL AND GLOBUOL The fraction boiling at 

 190 and up was placed in a shallow dish and allowed 

 to stand for several days until crystals began to sepa- 

 rate: these were removed, dried on a porcelain plate, 

 dissolved in alcohol and after adding enough water to 

 produce turbidity allowed to evaporate spontaneously 

 until crystals separated. After another recrystalli- 

 zation soft white flaky crystals were obtained which 

 gave the following constants: 



B. p. = 255 M. p. = 80 D 20 = 0.988* 

 [a] 2 D = +31. 21 in 12 per cent chloroform solu- 

 tion. 



Assuming the formula proposed by Semmler and 

 Tobias, 1 namely, a bicyclic alcohol with an unsaturated 

 grouping, the theoretical molecular index of refraction 

 would be 68.069; the observed molecular index of 

 refraction was 68.001. The acetate prepared by a 

 mixture of acetic anhydride and sodium acetate gave 

 constants identical with those obtained by Tobias and 

 Semmler. This and the general properties of the body 

 seemed to indicate that we were dealing with an alco- 

 hol rather than an oxide as suggested by Baker and 

 Smith. 



In the higher boiling portions a body corresponding 

 to globuol was separated. Semmler and Tobias con- 

 sider that this body bears the same relation to eudesmol 

 that borneol bears to isoborneol. 



Considering the formulas of the two alcohols to be 



i Semmler and Tobias. Ber.. 43 (2). (1913), 2026. 

 (5) 



