JACKSON AND KOCH. TRIBROMDINITROBENZOL. 121 



the isolation of the following products of the action of sodic ethylate 

 on tribromdinitrobenzol, melting jioint 192°, when absolute alcohol and 

 benzol are used as the solvents, and the mixture is allowed to stand at 

 ordinary temperatures : — 



(1) Broradinitroresorcine diethylether CoHBr(OCoH5)o(N02)2, melting 

 at 184°, (OCoH5).3l,5,Br3,(N02)22,4. 



(2) Broradinitroresorcine diethylether CcHBr(0C2H5)2(N02)>, melting 

 at 92°, (OC2H5)2l,3,Bro,(N02)22,4- 



(3) Tribromnitrophenol C6HBr3(N02)OH, melting at 90°, Bra 1,3,5, 

 ^0.2,0 114. 



(4) Dinitroresorcine monoethylether C6H2(OC2H5)OII(NOo)2, melting 

 at 77°, (OC2H5)l,OH5,N022,4. 



(5) Dinitrophloroglucine triethylether Con(OC2ll5)3(N02)2, melting at 

 105°, (OCori5)3l,3,5,(N02)22,4. 



These products indicate that there are three primary reactions, when 

 sodic ethylate acts on tribromdinitrobenzol. These are, Reactions I. and 

 II., consisting in the replacement of two atoms of bromine by two ethoxy 

 groups, producing the two isomeric broradinitroresorcine diethylethers 

 (1) and (2), and Reaction III., in which one uitro group is replaced by 

 one hydroxyl group (or by an ethoxy group followed by saponification) 

 giving the tribromnitrophenol (3). There are also two secondary reac- 

 tions owing to the further action of sodic ethylate on the products of 

 Reactions I. and II. ; first, the replaceraent of the bromine in the brora- 

 dinitroresorcine diethylether (1) by an atora of hydrogen (followed by 

 partial saponification) giving the dinitroresorcine monoethylether (4) ; 

 and secondly, the replacement of the bromine in the bromdiuitroresorcine 

 diethylether (2) by an ethoxy group giving the dinitrophloroglucine tri- 

 ethylether (5). The saponification mentioned in this paragraph might 

 be brought about by the sodic hydrate formed from the sodic ethylate by 

 the water added in the course of the purification, but it seems to us more 

 probable that the phenols were formed by some sodic hydrate acting 

 directly on the tribromdinitrobenzol, since the ethers of the phenols 

 seemed decidedly stable, when treated with an alkali. 



The following estimations of the approximate yields of the products 

 give a rough idea of the extent to which each of the three primary 

 reactions ran : — 



Reaction I., forming substances (1) and (4) . . . 28 per cent. 



Reaction II., forming substances (2)and (5) . . . 38 per cent. 



Reaction III., forming substance (3) 1 per cent. 



Total G7 per cent. 



