HILL AND CORNELISON. — CROTONOLACTONES. 39 



residue soon crystallized in long slender prisms, which when recrys- 

 tallized from ligroin melted at 52-53°, and in other respects showed 

 the behavior of the a-chlorcrotouolactone. The /38-dichlorpyromucic 

 acid, like the corresponding acid containing bromine, may, therefore, 

 be made to yield either the a- or the /3-chlorcrotouolactone. While 

 we had no doubt that the •yS-dichlorpyromucic acid would show an 

 essentially different behavior, and would yield, when treated in this 

 way, the same n-chlorcrotonolactone which it gives when heated with 

 acids, we thought it worth while to establish the fact by experiment. 

 The yS-dichlorpyromucic acid was therefore treated with bromine in 

 a feebly alkaline solution, and the oil, which was thus formed, was 

 then reduced with zinc dust and glacial acetic acid. It was easy to 

 isolate, as before, the a-chlorcrotonolactone melting at 52-53° with its 

 characteristic properties. 



a-PHENOXY-/3-BROMCROTONOLACTONE. 



Many years ago Hill and Stevens * prepared from mucobromic 

 acid, by the action of potassic phenylate, a derivative of mucobromic 

 acid, in which one atom of bromine was replaced by the phenoxy 

 group, and to which they gave the name mucophenoxybromic acid.f 

 They showed that this acid had the same general structure as the 

 mucobromic acid, in that it could be converted by oxidation into a 

 phenoxybrommaleic acid, and that it yielded on decomposition with 

 alkalies a phenoxybromacrylic acid. The stability of the latter acid 

 in alkaline solution led them to the conclusion that it contained the 

 phenoxy group in the a position. Although none of the substituted 

 crotonolactones which we had studied could directly be converted into 

 the salts of the oxy-acids, it seemed to us probable that the corre- 

 sponding bodies containing the phenoxy group would react more 

 smoothly. As the preliminary experiments which we made on the 

 action of sodic or potassic phenylate upon the dibromcrotonolactone 

 gave us little hope that the desired bodies could be made in this way, 

 we turned to the mucophenoxybromic acid, and found that the a-phe- 



* These Proceedings, XIX. 262. 



t Beilstein in the second edition of his " Handbuch der organisehen Chemie " 

 (II. 429) has seen fit to change this name to phenoxymucobromic acid. It is 

 quite possible that we might have selected a better name for our new body, but 

 it certainly would be difficult to find one more misleading than that which 

 Beilstein has chosen to give it. Whatever else it may be, it certainly is not a 

 phenoxymucobromic acid. H. B. H. 



