10 BIBLIOGRAPHY OF 



chloric! a compound, Cg He CL O2, melting at 101° is formed, which 

 proves the presence of the hydrox}^ and carboxyl groups, and also that 

 the fourth oxygen atom is united to carbon. Dehydracetic ester, Cg 

 H7 (C2 H5 ) O4, melts at 91.6°, dehydracetanilid, Cg H7 (N HCe H5 ) O3, 

 fuses at 115 , and chlor-dehj-dracetic acid, Cg Hy CI O4, fuses at 93°, 

 brom-dehj^dracetic acid, Cg H7 Br O4, was also described. The formula 

 assigned to dehydracetic acid is CH3 OH CO, H 



CO C = C 



CH, -C = CH 



WISLICENUS, J., 1877. 



Ann. Chem. 186, 161-228 ; J. Chem. Soc. 32, 432. 



Acetoacetic Ester. 



A short review is given of the work done by different chemists on 

 the reaction between sodium and acetoacetic ester. The methylene 

 hydrogen atoms of acetoacetic ester can be replaced by alkyl groups 

 only by passing through the mono-sodium, mono-alkyl, and sodium- 

 alkyl compounds, in that order. Diethyl acetoacetic ester boils at 218° 

 and is not attacked by sodium even at 100° In the reaction between 

 sodium and acetic ester, sodium acetoacetic ester and sodethoxid are 

 formed, and if ethyl iodid be added now, ethyl-acetoacetic ester is 

 formed, upon some of which sodethoxid will instantly act and form 

 sodethylacetoacetic ester, which, in contact with ethyl iodid now gives 

 diethylacetoacetic ester. Frankland and Duppa wrongly attribute the 

 last named body to the first action of sodium on acetic ester. These 

 complications are due to not removing sodethoxid before adding ethyl 

 iodid. The saponification of acetoacetic ester derivatives yields either 

 substituted ketones and a carbonate, or substituted acetates and alcohol. 



CONRAD, M., 1877. 

 Ann. Chem. 186, 228-232 ; J. Chem. Soc. 32, 435 ; Jsb. Chem. 



1877, 689. 

 Acetoacetic Amyl Ester 



Amyl acetate treated with sodium produces acetoacetic amyl ester, 

 CH3 CO CH2 CO2 C5 Hii, with no evolution of hydrogen if cold, and 



