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CLOVER. 



and acetic ester, -sparingly so in ether and chloroform and almost insoluble 

 in petroleum ether. They are best purified by recrystallization from hot 

 acetic ester, from which solvent they separate on cooling as fine needles, 

 melting at 164°. 5 to 165 °.5. In most cases they were pure after the first 

 crystallization. In the condition in which they are encountered in the 

 oil, the crystals are colorless, hexagonal prisms generally of good size; 

 two of the largest weighed, when taken together, just 1 centigram. The 

 body is probably the same as that noted by Tschirch and Cremer and also 

 previously observed by Wallach in ele mi-oil. Analyses gave the following 

 results : 



(1) 0.1G67 gram substance gave 0.4322 gram CO. and 0.1607 gram H 2 0. 



(2) 0.0713 gram substance gave 0.1853 gram CO, and 0.0708 gram H,0. 



Required for C 10 H 18 O. 



Found 





(1) 



(2) 



Per cent 



Per cent 



Per cent 



C=70.59 



70.71 



70.87 



H=10.59 



10.71 



11.03 



The substance is probably a dihydroxy-phellandrene. That it is of 

 the simple formula given, rather than a polymer, is indicated by the 

 fact that it sublimes very readily when it is heated below its melting- 

 point. 



As to the physical constants of phellandrene, the values obtained from 

 XVI,A, purified, should be given preference. Those of several of the 

 other samples, most of which it will be seen later contain small amounts 

 of lsevo-limonene, are also given in the following table there being of 

 course very little difference except in the degree of rotation. 



Designation of 

 product. 



Boiling 



point 



complete. 



„ 30 



n 30 



"d 



Sp- gr., 



Boiling point at reduced 

 pressure. 



XVI.A, purified 

 V,A, purified 

 XIV.A, purified. _ 



o o 



172-173. 5 

 172-174 



o 

 129.8 

 122.6 

 105.1 

 113.5 



1. 4695 

 1. 4698 

 1. 4694 



1. 4696 



0. 8324 



.8322 

 .8330 



89°.3 to 90°.8, 56.5 millimeters. 

 82°.7 to 84°, 43.5 millimeters. 



XVIII, A, purified __ J 172-173. 5 



Two determinations each gave the specific gravity at ( . ) as being 

 '0.0075 less than that at ( 2 4 °). 



The boiling point of phellandrene is seen to be about 4° lower than 

 that of limonene; the specific gravity is a little less while the index of 

 refraction is somewhat higher. 



In discussing the constitution of phellandrene Wallach 25 has recently 

 deduced the molecular-refraction of the substance, deriving his number 



25 Loo. tit. 



