OP ARTS AND SCIENCES. 359 



had the characteristic odor of the tetrabromfurfuran, and crystallized 

 from hot alcohol in irregular plates, which melted at 75-76°. Analy- 

 sis showed this substance to be a trichlorbromfurfuran. 



I. 0.1749 grm. substance dried over H 2 S0 4 gave 0.4269 grm. AgCl 

 and AorBr. 

 II. 0.1411 grm. substance dried over H 2 S0 4 gave 0.3447 grm. AgCl 



The strongly acid filtrate from the trichlorbromfurfuran and unal- 

 tered trichlorpyromucic acid yielded on extraction with ether a crys- 

 talline acid which was readily soluble in water. The amount of this 

 acid was too small for analysis, but it was easily identified as dichlor- 

 maleic acid by the melting point of its anhydride, 119-120°.* 



The reaction had therefore taken place in accordance with the 

 following equations : 



C 5 HC1 3 3 4- Br 2 = C 4 CLBrO + C0 2 + HBr. 

 C 5 HC1,0 3 + 2 Br 2 + 3 H 2 = C 4 H 2 C1 2 4 + C0 2 + HC1 + 4 HBr. 



Action of Nitric Acid. 



Trichlorpyromucic acid is but slowly attacked by nitric acid, and 

 prolonged heating with moderately strong nitric acid is needed for 

 complete oxidation. Even after heating the acid for six hours with 

 six times its weight of nitric acid (Sp. Gr. 1.42) diluted with an equal 

 weight of water, a portion of the trichlorpyromucic acid escaped oxi- 

 dation. Carbonic dioxide was slowly given off, and a small quantity 

 of an insoluble oil was formed, which had a peculiar penetrating odor 

 not unlike that of substituted furfuran derivatives. Its quantity was 

 too small to admit of its identification. In solution we were able to 

 find nothing but dichlormaleic acid, which we purified through the 

 barium salt and identified by the melting point of its anhydride and 

 by analysis. 



0.1997 grm. substance dried over H 2 S0 4 gave 0.3086 grm. AgCl. 



Calculated for 

 C 4 H 2 C1 2 4 - Found. 



CI 38.38 38.20 



The reaction had therefore taken place in accordance with the fol- 

 lowing equation : 



C 5 IIC1 3 ; + 2 O + H 2 = C 4 H 2 CL0 4 + CO, + IIC1. 



* Ciamiciau and Silber, he. cit. 





