ACETO ACETIC ESTER 47 



If resorcin, Ce H 4 (OH) 2 , is used /9methyl-umbelliferone, 



C* TT OH^^ (CH 3 ): CH, 



<- _ 



QQ 



is formed which when treated with potassium hydroxid gives resaceto- 

 phenon, C 6 H 3 (OH) 2 CO CH 3 . The methyl ester and the carboxylic acid 

 of /3methyl-umbelliferone were formed. -/?-Di-methyl-umbelliferone, 



C 6 H 3 (OH) < 



was formed from resorcin and dimethyl- acetoactic ester. Metatoluene-/9- 



r\ / f^TT \ QTT 



methyl-coumarin, C6H 3 CH 3 <Q^_ _' CO 

 cresol, Ce H 4 OH CH 3 , and acetoacetic ester. 



r\ / f^TT \ QTT 



methyl-coumarin, C6H 3 CH 3 <Q^_ _' CO was ^ orme< ^ fro m para- 



PERKIN, Jr., W. H., 1883. 



Ber. 16, 2136-2140 ; J. Chem. Soc. 46, 64. 



Action of Ethylene Bromid on Acetoacetic and Benzoyl-acetic Esters. 



From acetoacetic ester, ethylene bromid and sodium, aceto-tri- 



CH 3 



CO 



I CH 2 



methylene carboxylic ester, C < I , is formed, which boils at 193 to 



I CH 2 

 C0 2 C 2 H 5 



195. The acid and the silver salt were obtained. Benzoyl-trimethy- 

 lene carboxylic ester and acid and benzoyl-trimethylene were also 

 produced. 



GEUTHER, A., 1883. 



Ann. Chem. 219, 119-128 ; J. Chem. Soc. 46, 836 ; Ber. 16, 2290 ; 

 Jsb. Chem. 1883, 1065. 



Constitution of Acetoacetic Esters and of Benzene. 



The formation of tri-brom- acetoacetic ester by Wedel and the forma- 

 tion of acetoacetic ester from acetic ester are cited as proof of the 

 formula CH 3 COH : C H CO 2 C 2 H 5 and against CH 2 : COH CH 2 CO 2 



