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

The synthesis of 2-phenoxyalkanoic acids (ethanoic, propanoic, butanoic) was realised by the reaction of ortho-hydroxybenzamide respectively N-phenyl-o-hy- droxybenzamide with -halogenated acids in aqueous sodium hydroxide solution. 2-o-(carbamoyl)phenoxy-2-methyl- and 2-o-(phenylcarbamoyl)phenoxy-2-met- hyl-propanoic acids were obtained by reaction of the appropriate amide with ace- tone, 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-phenylcarba- moyl)phenoxyalkanoic acids with hydrazine 2-2-(N-phenylcarbamoyl)phenoxyal- kanoic acids hydrazides were obtained, which are considered key intermediates for the synthesis of several series of new compounds. Schiff bases and N-imido-deriva- tives were obtained by condensation of hydrazide with substituted aromatic alde- hydes respectively maleic anhydride. The synthesized compounds were character- ized by physico-chemical methods (FTIR, NMR and mass spectrometry).