Open AccessThe synthesis and characterization of some ortho-substituted phenoxyalkanoic acids and their derivatives
Author(s) -
Alfa Xenia Lupea,
Iuliana Popescu,
C. Tarabasanu,
Ioana Maria Carmen Ienașcu,
Valentin Badea
Publication year - 2006
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc0612247l
Subject(s) - chemistry , hydrazide , amide , maleic anhydride , chloroform , ethyl acetoacetate , organic chemistry , sodium hydroxide , hydrazine (antidepressant) , acetone , propanoic acid , ethyl bromoacetate , medicinal chemistry , catalysis , polymer , chromatography , copolymer
The synthesis of 2-phenoxyalkanoic acids (ethanoic, propanoic, butanoic) was realized by the reaction of ortho-hydroxybenzamide respectively N-phenyl-o-hydroxybenzamide with ?-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 ?-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). .