Synthesis and hydrolysis of Erlenmeyer-Plöchl azalactones mediated by microwave radiation in domestic and dedicated ovens: undergraduate organic chemistry experiments

Química Nova

Universidade Federal da Bahia, Salvador, Brasil¹  Cunha, Silvio¹  Santos Filho, Raimundo Francisco dos¹  Dourado, Glauber Antonio Albuquerque¹  Riatto, Valéria Belli¹  Universidade Federal da Bahia, Salvador¹  Universidade Federal do Recôncavo da Bahia, Amargosa, Brasil¹ 

关键词: hypuric acid;    undergraduate organic chemistry experiment;    green chemistry.;   

DOI  :  10.1590/S0100-40422013000100032

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

This work describes a green chemistry experiment for the synthesis of Erlenmeyer-Plöchl azalactones mediated by microwave irradiation, employing both dedicated and domestic equipment. Hippuric acid was reacted with equimolar amounts of benzaldehyde, p-chloro-benzaldehyde or p-N,N-dimethyl-benzaldehyde in acetic anhydride as the solvent. Acid hydrolysis of obtained 4-benzylidene-2-phenyloxazol-5(4H)-one under microwave and convectional heating afforded Z-α-(benzoylamino)cinnamic acid at a 51-61.5% yield. The UV-Vis molecular spectra of 4-benzylidene-2-phenyloxazol-5(4H)-one and 4-(4'-N,N-dimethylbenzylidene)-2-phenyloxazol-5(4H)-one were obtained in ethanol, CH2Cl2 and DMSO and bathochromic shift was observed for the latter azalactone.

【 授权许可】

Unknown