100 BIBLIOGRAPHY OF 



and a subsequent separation of hydrochloric acid forming a lactone. 



In the formation of sodacetoacetic ester an aldol polymerization is 



supposed to take place first, the product of which is acted upon by 



/ OC 2 H 5 

 sodium thus: 2 CH 3 CO 2 C 2 H 5 =CH 3 C- -CH 2 CO 2 C 2 H 5 , then 



-OH 

 ^OC 2 H 5 



sodium forms CH 3 C CH 2 CO 2 C 2 H 5 , which is again acted upon by 



\ONa 



sodium to form CH 3 CONaCHCO 2 C 2 H 5 , NaOC 2 H 5 and H. If sodium 

 be made to act on acetoacetic ester, CH 3 COCHNaCO 2 C 2 H 5 is formed 

 but the sodium is immediately attracted to the carbonyl group and it 

 changes to form CH 3 CONa:CHCO 2 C 2 H 5 . When this last compound 

 is treated with an alkyl iodid, C 2 H 5 i for example, there is an addition 

 product formed and as the group CONa=is more positive than the 

 group=CH , the iodin add to the former and the ethyl adds to the 



/ONa 



= CH group forming CH 3 C CH (C 2 H 5 ) CO 2 C 2 H 5 from which 



\ i. 



sodium iodid separates leaving CH 3 COCH (C 2 H 5 ) CO 2 C 2 H 5 . 



POLONOWSKY, M., 1888. 



Ann. Chem. 246, 1-32 ; J. Chem. Soc. 54 1067 ; Ber. 21, 636 (C). 

 Condensation of Glyoxal with Acetoacetic Esters. 



By treating a mixture of glyoxal, CHOCHO, and acetoacetic ester 

 with zinc chlorid two products are formed, (i) a part soluble in alkalis 

 which contains methyl-furfuran carboxyacetic or sylvanecarboxyacetic 



acid, 0<^\9S 2 /oA :( ^>, wnich melts at 2 7- The normal 

 ^ (<~"- 3 ; ^ (<-U 2 -tl; 



and acid, methyl and ethyl esters were produced and described ; (2) a 

 part insoluble in alkalis which consists of a heavy oil and a crystalline 

 substance, both having the composition C I4 H l8 Oe- The oil is di-ethyl- 

 sylvane-carboxy-acetoacetic ester which is : 

 CH 3 



CO CH (CH 3 ) C 



i I >O 



CH C: (C0 2 C 2 H 5 ) C 



C0 2 C 2 H s 



