334 PROCEEDINGS OF THE AMERICAN ACADEMY 



5 parts of water. After the lapse of two hours, the action appeared 

 to be completed, although a few drops of oil were still suspended in 

 the clear solution. The products of the reaction were then extracted 

 from the diluted solution with ether, the residue obtained by the 

 evaporation of the ether pressed thoroughly with filter-paper and 

 dried at 100°. The dry residue was then repeatedly washed with 

 benzol in which chlorfumaric acid is but sparingly soluble. The 

 product thus obtained was readily soluble in water, almost insoluble 

 in benzol, melted at 188°, and contained the percentage of chlorine 

 required by chlorfumaric acid.* 



0.1089 grm. substance dried over H 2 S0 4 gave 0.1027 grm. AgCl. 



Calculated for 



C 4 H 3 C10 4 . Found. 



CI 23.59 23.31 



The reaction may therefore be represented, in part at least, by the 

 equation 



C 5 H 3 C10 3 + 30 = C 4 TI 3 C10 4 + C0 2 . 



Action of Bromine and Water. 



Since j3 brompyromucic acid in aqueous solution is readily con- 

 verted by an excess of bromine into mucobromic acid,f it seemed to us 

 of interest to study the behavior of the (3 chlorpyromucic acid under 

 the same conditions, since a product containing bromine and chlorine 

 might then be formed. The acid was therefore suspended in five 

 times its weight of water, and an excess of bromine at once added. 

 After heating for a short time a clear nearly colorless solution was 

 obtained, which was concentrated by evaporation on the water bath. 

 On cooling, the solution deposited a crystalline acid which was readily 

 soluble in hot water or hot benzol, and but sparingly soluble in these 

 solvents in the cold. The acid recrystallized from water formed thin 

 rhombic plates which melted at 120-121°, but this melting point could 

 easily be raised to 121-122° by recrystallization from benzol. 



An analysis of the substance dried over sulphuric acid showed that 

 it was the mucochlorbromic acid whose formation we had been led to 

 expect. 



0.2871 grm. substance gave 0.4486 grm. AgCl + AgBr. 



Calculated for 

 C 4 U 2 BrC10 3 . Found. 



Br+Cl 54.11 54.45 



* Kauder (Journ. f. prakt. Chem., [2], xxxi. 28) gives the' melting point of 

 chlorfumaric acid as 191°. 



t These Proceedings, xxi. 152. 



