340 PROCEEDINGS OF THE AMERICAN ACADEMY 



its calcium salt, in which it closely resembled the /3y dibrompyromucic 

 acid, gave fair ground for the conjecture that it had a similar struc- 

 ture. A study of its oxidation products showed that such was the 

 case, since we easily obtained from it mucochloric and dichlormaleic 

 acids. 



Action of Bromine and Water. 



If bromine is added to (By dichlorpyromucic acid suspended in 

 six or eight times its weight of cold water, oxidation rapidly ensues, 

 with the escape of carbonic dioxide. A slight excess of bromine was 

 added, and the reaction completed by the aid of heat. On cooling, the 

 solution solidified with the separation of colorless crystals, which when 

 recrystallized from water and finally from benzol melted at 124-125°, 

 and had the characteristic form of mucochloric acid. Analysis also 

 gave the proper percentage of chlorine. 



I. 0.2015 grm. substance dried over H.^SO^ gave 0.3408 grm. AgCl. 

 II. 0.2320 grm. substance dried over HgSO^ gave 0.3922 grm. AgCl. 



CI 



In this case the reaction may be represented by the equation 



C5H2CI2O3 + 2Bro + 2 H.O -r C.H.ClaOa + CO2 + 4 HBr. 



Action of Nitric Acid. 



Nitric acid acts but slowly upon the ^y dichlorpyromucic acid, and 

 for its complete oxidation we have found it necessary to take for one 

 part of the acid 3 parts of concentrated nitric acid (Sp. Gr. 1.42) 

 diluted with twice its weight of water. After boiling for five hours 

 the action appeared to be complete, and as the clear solution deposited 

 nothing on cooling we extracted it with ether. The ether left upon 

 evaporation a colorless crystalline mass, which proved to be a mixture 

 of two substances, one readily soluble, the other but sparingly soluble 

 in cold water. The sparingly soluble substance when recrystallized 

 from hot water was recognized by its crystalline form and by its 

 melting point, 124-125°, as mucochloric acid. The acid, which was 

 readily soluble in cold water, was neutralized with baric carbonate, 

 the barium salt precipitated from its aqueous solution by alcohol, and 

 the acid liberated from this purified barium salt again extracted with 

 ether. The crystalline acid left by the evaporation of the ether was 

 then dissolved in a small amount of water, and on standing well 



