HILL AND CORNELISON. — CROTONOLACTONES. 53 



form of small oblique prisms, which melt at about 16G°. Like muco- 

 bromamide it dissolves readily iu solutions of the alkaline hydrates, 

 and is reprecipitated unchanged if the alkaline solution is immediately 

 acidified. On boiling for some time with concentrated hydrochloric 

 acid, it is converted into mucochloric acid, as was shown by the melt- 

 ing point, 124°. 



MUCOPHENOXYBUOMIC AdD. 



Mucophenoxybromoxime, C 4 H 8 (OC H 5 )BrNO3. — We have found 

 that hydroxylamine readily reacts upon mucophenoxybromic acid, 

 and that the corresponding oxime is formed both in alkaline and acid 

 solution. It may conveniently be prepared by adding to a solution of 

 the acid in 20 times its weight of 50 per cent methyl alcohol the 

 equivalent amount of hydroxylamine hydrochlorate. After standing 

 for a short time at ordinary temperatures the oxime begins to sepa- 

 rate in beautiful clusters of long needles, and in a few hours the 

 reaction is completed. 



0.2717 grm. substance gave 0.1791 grm. AgBr. 



Calculated for C 4 H 3 (0C e II 5 )BrN0 3 . Found. 



Br 27.97 28.04 



Mucophenoxybromoxime is readily soluble in alcohol or ether, and 

 insoluble in chloroform or benzol. It is almost insoluble in cold 

 water, dissolves but sparingly in boiling, and separates apparently 

 unchanged if the solution is quickly cooled. On long boiling it is 

 decomposed, and the solution then contains ammonia and phenoxy- 

 brommaleic acid. The solution was acidified with hydrochloric acid, 

 extracted with ether, and the acid removed from the ethereal solution 

 with sodic carbonate. The alkaline solution then gave on acidification 

 small clustered needles, which melted at 104-105° when rapidly 

 heated. On sublimation a crystalline body was obtained which melted 

 at 91°. According to Hill and Stevens, phenoxybrommaleic acid, 

 when quickly heated, melts at 104-105°, and we found that then- 

 acid when sublimed yielded the anhydride melting at 91°. The oxime 

 shows great variation in melting point (120-135°), according to the 

 mode of heating, and we have not yet been able to show that it is 

 converted into the phenoxybrommaleinimide by heat. The melted 

 body did not solidify on further heating, nor did it crystallize on 

 cooling. 



