OP ARTS AND SCIENCES. 31") 



This decomposition of the trinitrophloroglucine triphenylether 

 by sodic ethylate calls to mind the behavior of esters with another 

 alcohol and a small quantity of an alcoholate, as studied by Purdy * 

 and Peters,! especially as our ether approaches the esters on ac- 

 count of the marked acid properties of the trinitrophloroglucine. 

 Kossel and Kriiger $ have also found that sodic ethylate converts 

 salol into salicylic ester (or acid), and sodic phenylate, and that 

 glycerids are decomposed by sodic ethylate in a similar way, a 

 result which is confirmed by Obermuller.§ 



Action of Sodic Ethylate on Tribromnitroresorcine Diethylether. 



Early in our work with the tribromnitroresorcine diethylether 

 melting at 101° we noticed that, although it was not acted on by a 

 cold solution of sodic ethylate in alcohol, it was attacked if heated 

 with such a solution, but our attempts to study this reaction were 

 baffled for a long time by the difficulty in removing from the crys- 

 talline product the large amount of tarry matter which was formed 

 at the same time, even constituting almost the whole of the mass, 

 if the heat was not applied cautiously. After many experiments 

 we succeeded in obtaining a satisfactory result by proceeding as 

 follows. 13 gr. of tribromnitroresorcine diethylether were cov- 

 ered with absolute alcohol, and an alcoholic solution of sodic 

 ethylate added. The flask containing the mixture was, after fitting 

 it to a return condenser, immersed in a beaker of cold water, which 

 was heated slowly. As the temperature rose the substance went 

 into solution with a pale reddish color, and in a few minutes after 

 that there was a sudden change, the solution becoming almost black, 

 although the reaction was not at all violent. At this point the 

 heating must be stopped to avoid the formation of a large quantity 

 of the tarry impurity. The contents of the flask, which had a pe- 

 culiar aromatic odor not belonging to the compound we have isolated, 

 was allowed to evaporate to dryness spontaneously, and the residue 

 washed several times with cold water, which was found to contain 

 sodic bromide. The water left undissolved a most unpromising 

 tarry mass with almost no sign of crystalline form, but by extracting 

 it with hot ligroine a crystalline substance was obtained, which was 

 purified by repeated crystallization from hot alcohol with the aid of 



* Ber. d. ch. Ges., XX. 1554. \ Zeitschr. Physiol Chem., XV. 321. 



t Ann. Chem , CCLVII. 353. § Ibid , XVI. 152. 



