ACETO ACETIC ESTER 12^ 



has been further studied. When treated with formic or sulfuric acid 

 an isomer is formed, to which the formula, 



C6 H4 — C 



I I 



C6H4— C(OH)— CH, 



is provisionally given, and which is called isophenanthroxylene-aceto- 

 acetic ester; it melts at 177.° It forms a mono-acetyl derivative, C20 

 H15 (C2 H3 O) O4 , which melts between 165° and 170°, and a mono- 

 hydrazone, C20 H16 O3 (N2 HCe H5). No pyrazolone could be obtained 

 from this, and phenanthroxylene-acetoacetic ester does not react with 

 phenylhydrazin. With bromin the iso compound gave C20 H15 Br O4 . 

 When reduced the iso compound gave C20H16O3, which is also pro- 

 duced from the phenanthroxylene-acetoacetic ester by means of 

 hydriodic acid. This gave a phenylhydrazin derivative, C20 H16O2 

 (N2HC6H5). When treated with hydriodic acid the iso compound 

 gave C17 H12 O , which is the compound to which Japp and Streatfield * 

 gave the formula C14 Hjo O . It is probably a ketone containing the 

 carbonyl group in a penta-carbon ring. Treated with an alkali the iso 

 compound gave the iso-phenanthroxylene-acetoacetic acid, C18 H,2 

 O4 , which is mono-basic. The action of acetic, propionic, sulfuric, 

 alcoholic hydrochloric acids and of alcoholic potash and ammonia on 

 phenanthroxylene-acetoacetic ester was determined and an account 

 given of the experiments. The subject requires more study before the 

 composition of these bodies can be definitely settled. The formula 

 proposed for the iso compound explains some reactions but leaves 

 others quite unexplained. 



■ See page 39. 



CLAISEN, L. AND E. HORI, 1891. 



Ber. 24, 139-140; J. Chem. See. 60, 416. 



Action of Hydroxylamin on Acetoacetic Aldehyde. 



By this action a compound Cs H13 N3 O3 , was produced which 

 crystallizes in white needles, melting at 174.° It is sparingly soluble in 

 ether, benzene and chloroform. Other compounds which were expected 

 from this reaction were not obtained. 



