208 PROCEEDINGS OP THE AMERICAN ACADEMY 



readily soluble in water, but crystallizing from benzol by evapora- 

 tion in rosettes. The melting point of the recrystallized acid was 

 found to be 61°. An analysis showed that the percentage of 

 bromine contained in this acid agreed with that required by a 

 bromacetacrylic acid. 



0.1630 grm. substance gave 0.1594 grm. AgBr. 



Calculated for C 5 H 5 Br0 3 . Found. 



Br 41.45 41.62 



The oxidation had therefore taken precisely the same direction 

 as that followed by the analogous decomposition of methyl pyro- 

 mucic acid, and through this product of oxidation it will doubtless 

 be possible at some future time to fix the constitution of the brom- 

 methylpyromucic acid. A product apparently identical with this 

 we have also obtained by the action of dilute nitric acid. 



The insoluble product formed at the same time with the brom- 

 acetacrylic acid we unfortunately have not been able to study fur- 

 ther. It is not acid in its character, contains a large amount of 

 bromine, and crystallizes from benzol in long colorless prisms, 

 which melt at 90-91°. 



<»-Brommethylpyromucic Acid. 



Although bromine in acting upon methylpyromucic acid at ordi- 

 nary temperatures enters at once the furfuran ring, at the tempera- 

 ture of boiling carbonic disulphide or chloroform it attacks chiefly 

 the methyl group, and a bromine derivative is formed in consider- 

 able quantity which differs wholly in its properties from the acid 

 just described. The reaction is not perfectly simple, for we have 

 found that we could obtain the best yield of the new product by 

 using twice the theoretical quantity of bromine. We have dis- 

 solved the methylpyromucic acid in six times its weight of chloro- 

 form and slowly added to the boiling solution two molecules of 

 bromine diluted with its own weight of chloroform. The evolu- 

 tion of hydrobromic acid at once begins, and frequently before the 

 bromine is all added a heavy crystalline body separates from the 

 hot solution. When the reaction is over, the chloroform is well 

 cooled, the crystalline product, which amounts to about sixty per 

 cent of the weight of methylpyromucic acid taken, filtered off, and 

 washed with cold chloroform. It may then be recrystallized from 

 boiling chloroform or benzol. 



