JACKSON, DUNLAP. — BROMINE DERIVATIVES OF RESORCINE. 241 



solution when warmed with tribromresorcinediacetate deposited a pre- 

 cipitate which when filtered ofF soon turned black. This body was 

 undoubtedly the decomposition product of the sodium salt of tribrom- 

 resorcine. On account of the readiness, therefore, with which the 

 diacetate was saponified, it was not worth while to carry on this line 

 of investigation further. 



IVibromnitroresorctnediacetate, C 6 (NOo)Br 3 (OC 2 H 3 0) 2 . 



The diacetate of tribromresorcine when added to an excess of fuming 

 nitric acid immediately dissolved, and after standing several minutes 

 the solution became very warm and began to boil, the body in solu- 

 tion becoming completely oxidized; but if just before the oxidation 

 took place, when the solution was already hot, it was poured into an 

 excess of water, the resulting }'ellowish oil soon solidified. The sub- 

 stance was purified by crystallization from alcohol until it showed the 

 constant melting point of 161°, when it was dried at 100° and analyzed 

 with the following results : — 



0.1752 gram of the substance gave, by the method of Carius, 0.2086 

 gram of argentic bromide. 



Calculated for 

 C c N0 2 Br 3 (0C 2 H 3 0),. Found. 



Bromine 50.42 50.69 



The diacetate therefore behaves toward nitric acid like the tribrom- 

 ether rather than like the tribromphenol itself, for in the latter and in 

 the dibromether atoms of bromine are replaced by nitro groups, as 

 already described earlier in this paper. 



Properties. — The tribromnitroresorcinediacetate forms good-sized 

 prisms terminated by two planes at an obtuse angle to each other ; 

 it is very pale yellow, almost white, and melts at 161°. It dissolves 

 slowly in ligroin, is readily soluble in chloroform, benzol, and ether, 

 quite soluble in acetone, and tolerably soluble in carbonic di sulphide. 



In order to establish if possible the position of the three bromine 

 atoms in tribromresorcine, attempts were made to saponify the tribrom- 

 resorcinediethylether, which has the three bromine atoms arranged 

 symmetrically. When saponified in a sealed tube with aqueous hydro- 

 chloric acid, however, the product was a red body similar to that 

 formed by the action of water on tribromresorcine. Accordingly, in 

 hopes of a better result, dry hydrochloric acid gas was passed for one 

 hour over tribromresorcinediethylether heated in an oil bath to 200°, 

 but no saponification took place. 



vol. xxix. (n. s. xxi.) 16 



