The synthesis and characterisation of some ortho-substituted phenoxyalkanoic acids and their derivatives

Autor: VALENTIN BADEA, IOANA IENASCU, CORNELIU TARABASANU, IULIANA POPESCU, ALFA XENIA LUPEA
Jazyk: angličtina
Rok vydání: 2006
Předmět:
Zdroj: Journal of the Serbian Chemical Society, Vol 71, Iss 12, Pp 1247-1261 (2006)
Druh dokumentu: article
ISSN: 0352-5139
Popis: The synthesis of 2-phenoxyalkanoic acids (ethanoic, propanoic, butanoic) was realised by the reaction of ortho-hydroxybenzamide respectively N-phenyl-o-hydroxybenzamide with a-halogenated acids in aqueous sodium hydroxide solution. 2-[o-(carbamoyl)phenoxy]-2-methyl- and 2-[o-(phenylcarbamoyl)phenoxy]-2-methyl- propanoic acids were obtained by reaction of the appropriate amide with acetone, chloroform and sodium hydroxide. Ethyl esters of 2-phenoxyalkanoic acids were obtained by the reaction of the amide with ethyl esters of a-halogenated acids in different reaction media. Starting from the ethyl esters of 2-[2-(N-phenylcarbamoyl) phenoxy]alkanoic acids with hydrazine 2-[2-(N-phenylcarbamoyl)phenoxy]alkanoic acids hydrazides were obtained, which are considered key intermediates for the synthesis of several series of new compounds. Schiff bases and N-imido-derivatives were obtained by condensation of hydrazide with substituted aromatic aldehydes respectively maleic anhydride. The synthesized compounds were characterized by physico-chemical methods (FTIR, NMR and mass spectrometry).
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