OF ARTS AND SCIENCES. 163 



IX. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ON THE REDUCTION OF CAMPHOR TO BORNEOL. 



By C. Loring Jackson. 



Communicated November 12th, 1884. 



In 1883, Menke and I published a paper* entitled " A New Method 

 of Preparing Borneol from Camphor," in which we described, first, the 

 complete reduction of camphor to borneol by sodium and moist toluol ; 

 secondly, a convenient practical method for making borneol by the action 

 of one and a third times the theoretical amount of sodium on an alco- 

 holic solution of camjjhor, and purifying the product by crystallization 

 from hot alcohol ; and thirdly, explained the formation of the borneol 

 by the followiug reaction : — 



C,„H,,0 + H, = C.JI.p. 



In the first number of the Monatshefte fiir Chemie f for this year, 

 Kachler and Spitzer published an examination of our method, which 

 led them to the conclusion that it was worthless, since in three experi- 

 ments they obtained products, the larger part of which melted from 

 179'' to 181°, and in no case higher than 185° even after fractional 

 crystallization and sublimation (borneol melts at lOOi") ; while 

 another set of experiments showed that as much as 82.8'J^ of the hy- 

 drogen evolved by the sodium in one case, and oiA^/o in another, 

 escaped in tlie free state. They also determined how much borneol 

 had been formed in one of their experiments, by converting the crude 

 product into chloiides, and determining the chlorine, which showed 

 22.8% of borneol to 77.2*^ of unaltered camphor; and therefore doubt 

 whether the formation of borneol was due to reduction by nascent 



* Tlicse Proceedings, Vol. XVIIL p. 93. 

 t Monatsliefte fiir Chemie, No. 5, p. 50. 



