72 PROCEEDINGS OF THE AMERICAN ACADEMY 



after treatment with dilute alcohol to destroy the remainder, the pro- 

 duct of the reaction thoroughly washed with water ; tlie yellowish 

 viscous mass thus obtained was oxidized with chromic anhydride, and 

 upon subliming the product, after removing the portions soluble in 

 water and sodic hydrate, yellow needles were obtained which melted 

 at 273°, and gave with zinc-dust and sodic hydrate a red color; they 

 were therefore anthrachinone. 



0.5745 gr, of the substance gave on combustion 1.7000 grs. CO, 

 and 0.2180 gr. H,0. 



The anthrachinone was further converted into the bromine com- 

 pound, which, by fusion with potassic hydrate yielded alizarine.* 



A second portion of the orthobrombenzylbromide treated with 

 sodium, and afterward freed from it in the same way, was distilled 

 with steam for a long time ; a white substance passed over solidifying 

 in part in the condenser, which was proved to be dibenzyl by its odor, 

 its melting-point 52°, and the following analysis : — 



0.2435 gr. of the substance gave on combustion with PbCrO^t 

 0.8240 gr. CO2 and 0.1700 gr. H^O. 



100.00 100.02 



No anthraceiiedihydride could be found in the distillate with steam, 

 although it was carefully searched for. 



The residue left in the flask, after the distillation with steam, was 

 a yellow viscous mass, which can be most conveniently purified after 

 distillation per se, as this destroys the greater part of the viscous 

 substances containing bromine, which render the extraction with a 

 solvent toilsome and unsatisfactory. The distillate, which passed over 

 without a pause from 260° to redness, consisted of a solid mixed with 

 oil, and had a very disagreeable rank smell, different from that of the 



* A preliminary notice of the work up to this point was published, Bar. d. 

 ch. G., 71), p. 1965. 



t Owinp to the case with wliich the substance sublimes, great diflSculty waa 

 encountered in getting a satisfactory combustion. 



