JACKSON AND COHOE. — METADIBROMDINITROBENZOL DERIVATIVES. 81 



Properties of the Dinitroresorcine Diphenylether, 

 C 6 H 2 (OC 6 H s ) 2 (N0 2 ) 2 . ((OC 6 H 5 ) 2 1. 3. (N0 2 ) 2 4. 6.). 



This substance, when crystallized from a mixture of benzol and alco- 

 hol, forms slender white prisms terminated by one slanting plane, or, 

 when better developed, by two planes meeting at a very obtuse angle 

 and modified by several smaller ones, so that a blunt end is formed. It 

 melts at 129°. It is freely soluble in benzol; soluble in cold toluol or 

 chloroform, or in alcohol, ligroin, or acetone when these solvents are hot; 

 slightly soluble in ether or amyl alcohol. The best solvent for it was 

 either dilute alcohol, or ligroin containing a little benzol. 



Some experiments were tried to determine whether the phenoxy 

 groups in the diphenoxydiuitrobenzol could be replaced by malonic ester 

 radicals (CH(COOC 2 H 5 ) 2 ), as a replacement of this sort had been ob- 

 served in the case of dichlordiphenoxyquinone.* The solid diphenoxy- 

 dinitrohenzol was dissolved in an alcoholic solution of sodic malonic ester, 

 and the mixture allowed to stand at ordinary temperatures over night ; 

 afterward it was treated with dilute sulphuric acid, which precipitated 

 an oil, and showed that phenol had been set free by the strong smell of 

 this substance. The oily precipitate, after washing with water, was 

 extracted with ether, which removed from it a pale yellow oily substance ; 

 but as this did not solidify even after standing for several months, we 

 tried to determine its nature by the analysis of a salt. A specimen of 

 the oil was dissolved in alcohol and treated with an aqueous solution of 

 sodic hydrate, which threw down a bright red precipitate ; this was 

 washed with benzol, dried in vacuo, and analyzed, with the following 

 results : — 



I. 0.1383 gram of the substance gave 0.0191 gram of sodic sulphate. 

 II. 0.1476 gram of the substance gave 0.0228 gram of sodic sulphate. 



Calculated for Found. 



C 6 Hj(N0 2 ) 2 OC 6 H 5 CNa(COOC 2 II-),. I. II. 



Sodium 5.23 4.47 5.01 



The results of these analyses, in connection with the elimination of 

 phenol, prove that the reaction has run as was expected. The phenoxy- 

 dinitrophenylmalonic ester separated from the salt as an oil, and there- 

 fore we did not think it worth while to attempt a more careful study 

 of it. 



* Jackson and Grindley, These Proceedings, XXX. 425. 



VOL. XXXVI. — 



