HILL AND CORXELISON. — CROTONOLACTONES. 35 



under a pressure of 18 mm. at 114—115° without uoticeable decompo- 

 sition. With aqueous alkalies it behaves like the corresponding bro- 

 mine compound, and gives a bright yellow solution. Hydroxvlamine 

 has no action upon it, and phenylbydrazine removes chlorine without 

 forming any crystalline product. Aniline when added to its solution 

 in dilute alcohol gives the highly crystalline a-phenylamido-/3-chlorcro- 

 tonolactone. Hydriodic acid gives at 100° the a-iod-/3-chlorcrotono- 

 lactone. 



Action of Oxidizing Agents. 



a-/3-Dichlorcrotonolactone is oxidized with even more difficulty than 

 the corresponding dibromlactone. After boiling for several hours with 

 eight times its weight of concentrated nitric acid (sp. gr. 1.42), a 

 large part of the lactone remained unaltered, and could be recovered 

 by distillation with steam. The aqueous solution was then evaporated 

 to dryness on the water bath, and the crystalline residue treated with 

 small quantities of cold water. Mucochloric acid was then left behind, 

 which after recrystallization from hot water melted at 124-125°. 

 The cold water had taken up a small quantity of a readily soluble acid, 

 which undoubtedly was dichlormaleic acid. Since mucochloric acid 

 yields dichlormaleic acid on oxidation with nitric acid, although it is 

 attacked with more difficulty than mucobromic acid, it did not seem to 

 us worth while to take further steps for its preparation in larger quan- 

 tity and identification. Bromine dissolved in concentrated hydro- 

 chloric acid oxidizes the dichlorlactone, although in this case also Ions 

 continued boiling is required to complete the react'on. 



Action of Aniline. 



Aniline readily reacts upon the a/3-dichlorcrotonolactone at ordi- 

 nary temperatures, and forms the a-phenylainido-/3-ohlorcrotonolactone. 

 The reaction runs best with a dilute solution in 50 per cent alcohol, 

 and on standing the product separates in broad glistening leaflets, 

 which are more or less highly colored. This color may be removed 

 by recrystallization from glacial acetic acid or from alcohol. 



0.1491 grm. substance gave 0.1011 grm. AgCl. 



Calculated for C in II 8 ClNO,. Found. 



CI 16.91 16.76 



o-Phenylamido-/3-chlorcrotonolactone is quite readily soluble in boil- 

 ing alcohol, and but sparingly soluble in cold. It also dissolves quite 

 freely in boiling chloroform or benzol, more sparingly in ether or 



