ACETO ACETIC ESTER 99 



BEYER, C. AND L. CLAISEN, 1888. 



Ber. 21, 1697-1705. 

 Mixed Azo Compounds. 



In this article some azo compounds are described which are formed 

 from acetoacetic esters. 



GRIESS, P. AND Q. HARROW, 1888. 



Ber. 21, 2740-2743 ; J. Chem. Soc. 54 ^3 1 3- 

 Action of Acetoacetic Ester on Hexamethylenetetramin. 



When acetoacetic ester acts on hexamethylenetetramin, (CH 2 ) 6 N 4 , 

 in presence of zinc chlorid, lutidin-di-carboxylic ester and hydro- 

 lutidin-di-carboxylic ester are formed. The latter, C 5 NHH 2 (CH 3 ) 2 

 (CO 2 C 2 H 5 ) 2 , melts at 170, is neutral and is considerably decomposed 

 upon being distilled. Treated with hydrochloric acid it gives two pro- 

 ducts, the mono- and di-ethyl esters of lutidin-dicarboxylic acid. 



MICHAEL, A., 1888. 



J. prakt. Chem. 145.473-530; Am Chem. J. 10, 158-160; J. Chem. 

 Soc. 54, 1054 ; Ber. 21, 530 (C) ; Bull. Soc. chim. 5. 690. 



Constitution of Sodacetoacetic Ester. 



By the action of chlor : carbonic ester on sod acetoacetic ester, carb- 

 ethoxacetoacetic ester was produced which boils unchanged at 127 at 

 i7m.m. pressure. No sodium derivative of this could be prepared, con- 

 sequently it was considered to be an isomer of aceto-malonic ester, 

 which does easily form a sodium derivative, and its formation was 

 supposed to be thus : CH 3 CONa:CHCO 2 C 2 H 5 +ClCO 2 C 2 H 5 =CH 3 CO 

 (CO 2 C 2 H 5 ) : CHCO 2 C 2 H 5 + NaCl. In the author's opinion acetoacetic 

 ester itself is a ketone. He gives as a formula for benzalacetoacetic 

 ester CH 3 C : C ' CO 2 C 2 H 5 , which explains its loss of ketone properties 



O CHC 6 H 5 



and to explain the reactions between bodies analogous to acetoacetic 

 ester such as levolinic acid, CH 3 COCH 2 CH 2 CO 2 H, and acetyl chlorid, 



he supposes an addition product thus : 



^O COCH 3 

 CH 3 CO--- etc.+CH 3 COCl=CH 3 C etc. 



