94 PROCEEDINGS OF THE AMERICAN ACADEMY 



us to become acquainted with the reduction of camphor; but, to our 

 great surprise, we were unable to find any description of experiments 

 on this subject, unless the statement in Beilsteiu's Handhuch der 

 Organischen Chemie, page 1763, that sodium amalgam does not act on 

 camphor, comes under this head. We were compelled, therefore, to 

 experiment ourselves, with the following result. 25 g. of camphor, 

 melting at 175°, were dissolved in moist toluol, and sodium and water 

 added at intervals, until a sample showed the melting-point of borneol, 

 197°-198°; the toluol was then driven off by heat, and a yellowish 

 white mass obtained, with the smell at once like camphor and pepper, 

 described as that of borneol. It was purified by sublimation, and 

 analyzed with the following results : — 



0.1642 g. of substance gave 0.4700 g. of carbonic dioxide, and 

 0.1772 g. of water. 



Carbon 

 Hydrogen 



The substance is borneol, therefore, and the reduction of the cam- 

 phor takes place, as was to be expected, according to the reaction. 



C,„II,,0 + II, = C,oH,,0. 

 Camphor. Borneol. 



The ease with which borneol was formed in this experiment led us 

 to the following method for making borneol from camphor, which 

 gives essentially the theoretical yield of nearly pure borneol with 

 remarkably little trouble. 



It consists in dissolving the camphor in about ten times its weight 

 of common alcohol, and adding one third * more than the amount of 

 sodium calculated from the reaction. The sodium is added in pieces 

 of somewhat less than a gramme at a time, and in working with quan- 

 tities not over ten grammes the action can be carried on in an open 

 flask without cooling. As soon as all the sodium has disappeared, 

 which takes less than three quarters of an hour with ten grammes of 

 camphor, part of the alcohol is distilled off, and water added, which 

 precipitates crude borneol. This is freed from sodic hydrate by wash- 

 ing witli water ; after which one crystallization from the smallest 

 possible amount of hot alcohol is sufficient to raise its melting-point 

 to 197°, that of borneol. In this way 10 g. of camphor yielded 9.5 g. 



* Probably a smaller excess of sodium would be sufficient. 



