160 PROCEEDINGS OF THE AMERICAN ACADEMY 



that formyl-acetic ether contains a hydroxyl group, 



HCOH 



II 

 HC-C0 2 R 



It seems to me, therefore, now only a question of time until it 

 will be generally accepted that the so called 1,3 and 1,4 dike- 

 tones, as acetylacetone, CH 3 COH=CH-CO-CH 3 , and acetonylace- 

 tone, CH 8 COH=CH-CH=COH-CH 8 , as well as acetacetic ether, are 

 hydroxylated compounds. 



Although v. Pechmann has shown that sodic formylacetic ether, 



HCONa 



II 

 HCC0 2 B 



when treated with benzoylchloride, is converted into 



HCOCOC 6 H 5 



II 

 HCC0 2 R 



i. e. that a direct replacement of the metal by benzoyl has taken 

 place, I have shown, on the other hand, in just as decisive a man- 

 ner, that, on treating acetoacetic ether salts, * 



CH3-COM 

 II 

 HCC0 2 R 



with acid chlorides, no direct substitution of the metal takes place. 



Furthermore, I have also shown some time ago that sodic suc- 

 cinosuccinic ether and sodic dihydrodioxypyromellithic ether, f 

 which substances are more closely related to acetoacetic ether than 

 formylacetic ether, behave towards alkyliodides and acid chlorides 

 in a different manner from sodic acetoacetic ether. This can only 

 be due to the fact that the double bond present in sodic acetacetic 

 ether is more reactive than in the other cases. 



V. Pechmann's experiments, J where he treats sodic acetacetic 

 ether in aqueous solution with benzoylchloride, and with chloro- 

 carbonic ether, are to be regarded as a repetition of my experi- 

 ments, since the process of the reaction must be the same whether 

 the operation be carried on in absolute ethereal or in aqueous so- 



* Ann. Chem. (Liebig), CCLXVI. 121. 



t Ibid., CCLVIII. 261. 



X Ber. d. chem. Ges., XXV. 410, 1045. 



