242 PROCEEDINGS OF THE AMERICAN ACADEMY. 



XL 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ON MUCOPHENOXYCHLORIC ACID. 

 By Harris Eastman Sawyer. 



Presented by H B Hill, February 14, 1894. 



It was found some years ago, by Hill and O. R. Jackson,* that 

 mucobromic acid was decomposed by treatment with baric hydrate, 

 and that the course of the reaction varied, according as the solution 

 was made strongly or feebly alkaline. In the first case, formic, di- 

 bromacrylic, and brompropiolic acids were formed. The product in 

 the latter case, as has been shown in a more recent investigation,! 

 was mucoxybromic acid. Hill and Stevens, pursuing the subject fur- 

 ther, studied the action of potassic phenylate on mucobromic acid, and 

 obtained a mucophenoxybromic acid whose constitution was established 

 by its conversion into phenoxybromacrylic and phenoxybrommaleic 

 acids. $ They made, however, no attempt to prepare the corresponding 

 series of chlorine compounds, because of the difficulties then attendant 

 on the preparation of mucochloric acid. As it has become possible to 

 obtain this acid in any desired quantity, it has seemed desirable to 

 continue this work, which is now of more interest because of the rela- 

 tionship between the substituted mucobromic and mucochloric acids, 

 and the recently described crotonolactones of Hill and Cornelison.§ 



The author would here express his deep obligations to Professor 

 H. B. Hill, at whose suggestion the research was undertaken ; and 

 to Mr. Howard Nash, for assistance in some of the analytical work. 



MUCOPHENOXYCHLORIC ACID. 



The following method has been found most advantageous for the 

 preparation of this acid. A solution of 17.6 grams of potassic hydrate 



* These Proceedings, Vol. XVI. p. 188. 

 t These Proceedings, Vol. XXII. p. 316. 

 \ These Proceedings, Vol. XIX. p. 262. 

 § These Proceedings, ante, p. 42. 



