JACKSON AND GAZZOLO. — NITRO COMPOUNDS. 269 



CH 3 OC 2 H 6 



\ / 



CH-NO 

 / \ 



N0 2 OH 



is a true stable acid ten times as strong as acetic acid, and it is fair to 

 suppose, therefore, that the substance 



OCH 3 



C 6 H 2 OCH 3 (N0 2 ) 2 NO 



\ 

 OH 



(formed by hydrochloric acid on our sodium salt, if it has Formula I.) 

 would also be comparatively stable, and not drop at ouce iuto the trini- 

 tranisol, which, as a matter of fact, is formed immediate]}' by the action 

 of hydrochloric acid on the colored compound. On the other hand, this 

 rapid decomposition by acid would be explained according to Formula 

 II. or III. by the strong tendency of quinoid bodies to pass iuto the hy- 

 droquinoid form, which might easily cause the splitting off of methyl 

 alcohol as soon as the atom of sodium was replaced by hydrogen. This 

 rapid decomposition with removal of methyl alcohol when the colored 

 bodies are treated with dilute hydrochloric acid recalls the similar behav- 

 ior of the dichlordimethoxyquinonedimethylhemiacetal ; * and the simi- 

 larity of these phenomena may tell in favor of classing the colored salts 

 with quinone derivatives, although the two reactions are not strictly 

 analogous. 



The third point in favor of Formula II. or III. is the replacement of 

 the two methyls in C c II.,(XO.,) :; OCTI 3 NaOCH 3 by benzyls when the com- 

 pound is soaked in benzyl alcohol, and the reverse change when the 

 benzyl compound is boiled with methyl alcohol. As under the same 

 conditions benzyl alcohol has no action on methyl picrate, or methyl 

 alcohol on benzyl picrate, it is obvious that the complete replacement of 

 one radical by the other here depends on the structure of the addition 

 product ; and, whereas Formula I. gives no reason why the change should 

 proceed beyond the methyl attached to the nitro group, it is easy to 

 see that in a substance constituted like Formula II. or III. any reagent 

 which affected one methyl would act in a similar way on the other, 

 so that the methyl compound would be completely converted into 

 C 6 H 2 (NO,) 3 OC 7 H 7 NaOC 7 H 7 . 



* These Proceedings, XXX. 431. 



