HILL AND CORNELISON. — CHOTONOLACTONE3. 43 



in hot alcohol, more sparingly in cold, very sparingly soluble in cold 

 ligroin, though more easily soluble in hot. When recrystallized from 

 small quantities of alcohol or from ligroin, it was obtained in radiating 

 needles which melted at 89-90°. 



0.2320 grm. substance gave 0.2631 grm. AgCl + AgBr. 



Calculated for C 4 H(0C u Hj)C10 2 Br. Found. 



CI + Br 39.89 39.53 



In the reduction of the mucophenoxychlorylbromide to the corre- 

 sponding lactone we followed the method which had already proved 

 convenient with the mucophenoxybroniylbromide. Zinc dust was 

 slowly added with careful cooling to the bromide dissolved in glacial 

 acetic acid. When the reduction was complete, the filtered solution 

 was diluted with water, and the crystalline body which was thus 

 thrown down was recrystallized from a small amount of alcohol. The 

 lactone which was precipitated by water amounted to 76 per cent of 

 the theoretical yield. 



I. 0.3243 grm. substance gave 0.6765 grm. C0 2 and 0.0995 grm. H 2 0. 

 II. 0.2256 grm. substance gave 0.1541 grm. AgCl. 



Calculated for Found. 



C 4 H,(0C H 5 )ClO,. I. II. 



C 57.02 56.89 



H 3.33 3.40 



CI 16.87 16.89 



The a-pheuoxy-/3-chlorcrotouolactone is readily soluble in ether, 

 chloroform, benzol, carbonic disulphide, and in hot alcohol or ligroin, 

 although but sparingly soluble in these solvents when cold, and almost 

 insoluble in water. From alcohol it crystallizes in six-sided plates, or 

 flattened prisms, which melt at 67-68°. In alcoholic solution it is 

 not affected by aniline at ordinary temperatures. When heated with 

 aqueous alkalies it is gradually carried into solution with the formation 

 of the salt of the corresponding oxy-acid. 



a-Phenoxy-fi-chlor-y-orycrotonic Acid, C 4 H 4 (OC 6 H 5 )C10 3 . — If the 

 a-phenoxy-0-chlorcrotonolactone is dissolved in a moderately dilute 

 solution of potassic hydrate by the aid of heat, and to the well cooled 

 solution a slight excess of hydrochloric acid is added, the phenoxyehlor- 

 oxycrotonic acid separates almost immediately in colorless pearly scales. 

 The crystals were removed by filtration, thoroughly washed with cold 

 water and dried over sulphuric acid. The substance was then analyzed 

 without further purification. 



