314 PROCEEDINGS OF THE AMERICAN ACADEMY 



until it showed the constant melting point 119-120°, which indi- 

 cated that it was trinitrophloroglucine triethylether, and this was 

 proved to be the case by the following analysis : — 



0.2080 gr. of the substance gave 22.5 c.c of nitrogen at a tem- 

 perature of 21° and a pressure of 759.3 mm. 



Calculated for 

 C 6 (OC,H 5 ) 3 (N0 2 ) 3 . Found.* 



Nitrogen 12.17 12.30 



The aqueous filtrate which contained the other products of the 

 reaction beside the trinitrophloroglucine triethylether gave no test 

 for sodic nitrite, even with starch paste, potassic iodide, and sulphu- 

 ric acid. It was acidified with dilute sulphuric acid and extracted 

 with ether, which left an oily substance solidifying after some time, 

 and smelling strongly of phenol. To prove that this was phenol, it 

 was dissolved in a large quantity of water and bromine water added 

 to the solution, which gave a white precipitate melting constant 

 after c^stallization from dilute alcohol at 92°, the melting point 

 given by Post for tribromphenol; as however both Korner and Sin- 

 tenis give 95°, we thought it necessary to analyze the substance, 

 which was done with the following result: — 



0.2803 gr. of the substance gave according to the method of Carius 

 0.4748 gr. of argentic bromide. 



Calculated for 

 C 6 H 2 Br 3 OH. Found. 



Bromine 72.51 72.07 



There can be no doubt, therefore, that the substance is tribrom- 

 phenol, and that the action of the sodic ethylate upon trinitrophlo- 

 roglucine triphenylether takes place according to the following 

 reaction : 



C 6 (OC 6 H 5 ) 3 (N0 2 ) 8 + 3NaOC 2 H 5 = C 6 (OC 2 H 5 ) 3 (N0 2 ) 3 + 3NaOC 6 H 6 . 



The bright red color observed in the solution was undoubtedly due 

 to some of the sodium salt of trinitrophloroglucine formed by the 

 action of the small amount of sodic hydrate, which it is almost im- 

 possible to exclude from sodic ethylate owing to the hygroscopic 

 nature of absolute alcohol. 



* This analysis has also been given earlier in this paper, where the compo- 

 sition of the triethylether is first determined. 



