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

Abstract

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). .

2-(3,4-Dichlorophenoxy)propionic acid

“…Phenoxy acids have been used as intermediates in the synthesis of many valuable target molecules (Lupea et al, 2006;Powers & Gotz, 2006). A series of aurones using phenoxy acids as intermediates has recently been synthesized and evaluated for insect antifeedant activity (Morimoto et al, 2007).…”

The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy)-N-phenylbenzamide derivatives

“…(13) , 1652 i, 1622 i, 1595 i, 1560 i, 1498 m, 1456 i, 1315 i, 1269 m, 1238 i, 1103 i, 1062 s, 1035 m, 950 s, 898 s, 765 m, (14) , 3178 m, l, 3099 s, 2979 s, 1681 i, 1598 m, 1548 m, 1483 s, 1446 i, 1398 m, 1269 m, 1226 m, 1093 s, 819 s, 750 s, 686 s, 542 s, 505 s, 462 s. 1 The experimental results suggested that the 5-chloro-2-(substituted alkoxy)--N-phenylbenzamide derivatives were readily purified. Their physical, chemical and spectral properties are given below.…”

“…Нова једињења су окарактерисана помоћу FTIR, 1 H-NMR, 13 C-NMR, MS и елементалном анализом. Eтил-естри су добијени реакцијом N-фенил-2-хидрокси-5-хлоро--бензамида и хлоро-супституисаних етил-естара 1-3 у етил-метил-кетону.…”

Synthesis and Characterization of Some New 2-Hydroxy-N-(3-Trifluoromethyl-Phenyl)-Benzamide Derivatives

“…In order to attain such active compounds, some orthosubstituted phenoxyalkanoic acids and their derivatives were synthesized and characterized [12,13].…”