ACETO ACETIC ESTER 119 



NEF, J. U., 1890. 



Ann. Chem. 258, 261-318, Am. Chem. J. 12, 379-425 ; J. Chem. 



Soc. 58, 983. 



Tautomeric Compounds. 



In this article acetoacetic ester is considered and the author decides 

 that it is a tautomeric compound ; that the sodium derivative has the 

 sodium combined to oxygen, thus : CH 3 CONa : CHCO 2 C 2 H 5 , but 

 that the ester itself and its alkyl derivatives have the ketonic oxygen, 

 thus: CH 3 COCHRCO 2 R. By treating sodacetoacetic ester with 

 benzoyl chlorid two compounds were produced, the principal one was 

 monobenzoyl-acetoacetic ester and the minor one was dibenzoyl-aceto- 

 acetic ester, CH 3 COC (COC 6 H 5 ) 2 CO 2 C 2 H 5 , which has never been 

 prepared before. It is very unstable and cannot be distilled even in 

 vacuum. 



BEHREND, R. AND PAUL ERNERT, 1890. 



Ann. Chem. 258, 360-362; J. Chem. Soc. 58, 1240; Ber. 23, 643(C). 

 Condensation of Carbarn id with Acetoacetic Ester. 



Carbamid condenses with sodacetoacetic ester to form a compound 

 C I3 H 22 N 2 O 7 Na 2 which is probably represented by the formula 



CH 3 CH 3 



CONa-HN-CO- NH CONa 

 CH 2 CH 2 



CO 2 C 2 H 5 CO 2 C 2 H 5 . 



It melts at 165 and is decomposed by water. It is also decomposed, 

 by passing carbon dioxid into its alcohol solution, into carbamid, 

 acetoacetic ester and sodium ethyl carbonate, NaC 2 H 5 CO 3 . 



