HILL AND C0RNEL1S0N. — CROTONOLACTONES. 51 



Mucochloric Acid. 



Toward hydroxylamine mucochloric acid behaves in essentially the 

 same way as mucobromic acid, although we have been unable as yet 

 to prepare the anhydride of the oxime, the body which was most 

 readily formed from mucobromic acid. The methyl ester of muco- 

 chloric acid when treated with ammonia gave mucochloramide without 

 difficulty. 



Mucochloroxime, C 4 H 3 C1 2 N0 3 . \ H 2 0. — Mucochloric acid was dis- 

 solved in a small amount of methyl alcohol, and one equivalent each 

 of hydroxylamine and sodic carbonate dissolved in a little water were 

 added. After the lapse of a few minutes the solution was acidified 

 with hydrochloric acid and the oxime immediately separated. Analy- 

 ses of the air-dried material (III.) or of the substance dried over sul- 

 phuric acid (I. and II.) showed that in each case one half-molecule of 

 water was retained. Since dichlormaleinimide was quickly formed at 

 temperatures below 100°, no attempt was made to dehydrate the sub- 

 stance by heat. 



I. 0.2220 grm. substance gave 0.2014 grm. C0 2 and 0.0471 grm. 

 H 2 0. 

 II. 0.2008 grm. substance gave 0.2992 grm. AgCl. 

 III. 0.1927 grm. substance gave 0.2851 grm. AgCl. 



IIL 



36.85 



Mucochloroxime crystallizes in slender felted needles, which are 

 readily soluble in alcohol or ether, and but sparingly soluble in cold 

 water. It dissolves readily in hot water, and if the solution is quickly 

 cooled, it separates apparently unchanged, but on heating for a short 

 time with water it is converted into the acid ammonium salt of dichlor- 

 maleic acid. The identity of the acid extracted by ether from the 

 acidified solution was established by the melting point of its anhydride 

 (119°). The melting point of the oxime cannot be determined with 

 precision, but it lies in the neighborhood of 90°. The melted oxime 

 passes into the dichlormaleinimide which solidifies and again melts at 

 175-177°. 



Methylester of Mucochloroxime, C 4 H 2 C1 2 N0 3 CH 3 . — The methyl 

 ester of mucochloroxime is formed when a cold solution of the oxime 



