312 PROCEEDINGS OF THE AMERICAN ACADEMY 



sodium salt even of the anilidodinitrobenzylmethylketone (the least 

 acid of all these substances) having been prepared and analyzed with 

 no especial difficulty ; it shows therefore a marked difference in this 

 respect from desoxybenzoiue (CyH^COCHgC^H.), the sodium com- 

 pound of which, according to Victor Meyer,* has not been isolated. 

 In fact, he thinks it probable that it may not exist in the free state, 

 and leaves it doubtful whether the syntheses of homologues of desoxy- 

 benzoiue are preceded by the formation of a sodium compound, as 

 with malonic or acetacetic ester, or whether the homologue is formed 

 direct by the removal of hydrogen and the halogen by sodic hydrate, 

 according to this reaction : 



C,H,COCHC,H, + CH3 + NaOH = NaT + HjO + C,H-COCHC,H.. 



I ' 'I ^ ' I 



[H T] CH3. 



The reason for this striking difference in acidity between the sub- 

 stituted benzylmethy] ketones and desoxybenzoiue can hardly be due 

 to the fact that the former contain the more active acetyl instead of 

 the benzoyl contained in the latter, although this may have some influ- 

 ence, but in my opinion is rather to be ascribed to the heightening of 

 the acid-producing power of the phenyl by the nitro groups which it 

 contains. The salts of the acetacetic or malonic esters are much more 

 stable than those of the ketones, as was to be ex^^ected, since in these 

 cases the hydrogen is exposed to the acidifying power of three radicals 

 (nitrophenyl and two carboxyls, or one carboxyl and an acetyl), and 

 their stability almost equals that of the salts of BischoflP'sf orthonitro- 

 benzoyl malonic ester, in which the nitrophenyl of my compounds is 

 replaced by the even more acid nitrobenzoyl. 



* Ber. fl. ch. G. 1888, p. 1291. 

 t Ann. Chem., ccli. 364. 



