228 PROCEEDINGS OP THE AMERICAN ACADEMY. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY 

 OF HARVARD COLLEGE. 



CERTAIN BROMINE DERIVATIVES OF RESORCINE. 

 By C. Lorixg Jacksox axd F. L. Duxlap. 



Presented February 14, 1894. 



The research described in the following paper was suggested by 

 the observation* tbat tribromnitroresorcine diethylether, when heated 

 with a solution of sodic ethylate, lost two atoms of bromine, which 

 were replaced by two of hydrogen, so tbat C 6 Br 3 N0 2 (OC 2 H 5 ) 2 was 

 converted into C 6 BrH 2 N0 2 (OC 2 II 5 ) 2 . Considering the easy removal 

 of these two atoms of bromine, it seemed possible that the tribrom- 

 resorcine diethylether, which differs from it only in the absence of the 

 nitro group, might behave in a similar way. This expectation has not 

 been fulfilled, as our experiments have shown that tribromresorcine 

 diethylether does not give up bromine to sodic ethylate at the boiling 

 point of alcohol, and that the dibrom ether is not attacked below 200°, 

 and therefore is, if anything, more stable than the symmetrical tri- 

 brombenzol, which according to Blau t is slowly converted into di- 

 bromanisol at temperatures of 120° to 130°. The behavior of free 

 tribromresorcine was next studied, and it was found that bromine 

 could be removed with great ease, even water at its boiling point 

 decomposing this substance, while solutions of sodic carbonate, or 

 sodic hydrate, or sodic ethylate dissolved in alcohol acted even more 

 readily. These results show that the ethoxyl groups do not loosen 

 the attachment of the bromine atoms to the benzol ring, whereas the 

 hydroxyl groups have as much of this loosening effect as do the nitro 

 groups in tribromdinitrobenzol. 



We have not succeeded in determining the nature of the organic 

 compounds produced by removing bromine from tribromresorcine, as 

 they were brown amorphous bodies, which could not be brought into 



* These Proceedings, XXVII. 315. 

 t Monatsh. f. Chem., VII. 630. 



