Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure

A convenient procedure for the direct esterification of cinnamic acids with phenols or 2-(N-phthalimido) ethanol is described. The method is simple and clean, environmentally friendly and high-yielding for both electron-releasing and electron-withdrawing substituted phenols. The heteropolyacid H 6P2...

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Detalles Bibliográficos
Autores principales: Ruiz, Diego Manuel, Romanelli, Gustavo Pablo, Bennardi, Daniel Oscar, Baronetti, Graciela Teresita, Thomas, Horacio Jorge, Autino, Juan Carlos
Formato: Articulo
Lenguaje:Inglés
Publicado: 2008
Materias:
Química
Acid catalysis
Cinnamates
Direct esterification
Heteropolyacid
Wells-Dawson acid
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/83477
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-83477
record_format dspace
spelling I19-R120-10915-834772023-08-15T18:34:14Z http://sedici.unlp.edu.ar/handle/10915/83477 Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure Ruiz, Diego Manuel Romanelli, Gustavo Pablo Bennardi, Daniel Oscar Baronetti, Graciela Teresita Thomas, Horacio Jorge Autino, Juan Carlos 2008 2019-10-17T14:16:41Z en Química Acid catalysis Cinnamates Direct esterification Heteropolyacid Wells-Dawson acid A convenient procedure for the direct esterification of cinnamic acids with phenols or 2-(N-phthalimido) ethanol is described. The method is simple and clean, environmentally friendly and high-yielding for both electron-releasing and electron-withdrawing substituted phenols. The heteropolyacid H 6P2W18O62·24 H2O was employed as catalyst, both bulk and supported on silica. No stoichiometric activation of the carboxyl group or condensing reagents is necessary. The effects of temperature, reaction time, amount of the catalyst used and mole ratio of the reactants on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % mass ratio of catalyst to reactant. Eighteen aryl and phthalimidoethyl cinnamates were obtained, yields ranged in 84-95% for most of the esters. The catalyst shown to be reusable for at least three times without occurring an appreciable loss of its activity. Facultad de Ciencias Agrarias y Forestales Centro de Investigación y Desarrollo en Ciencias Aplicadas Articulo Articulo http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) application/pdf 269-276
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Acid catalysis
Cinnamates
Direct esterification
Heteropolyacid
Wells-Dawson acid
spellingShingle Química
Acid catalysis
Cinnamates
Direct esterification
Heteropolyacid
Wells-Dawson acid
Ruiz, Diego Manuel
Romanelli, Gustavo Pablo
Bennardi, Daniel Oscar
Baronetti, Graciela Teresita
Thomas, Horacio Jorge
Autino, Juan Carlos
Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
topic_facet Química
Acid catalysis
Cinnamates
Direct esterification
Heteropolyacid
Wells-Dawson acid
description A convenient procedure for the direct esterification of cinnamic acids with phenols or 2-(N-phthalimido) ethanol is described. The method is simple and clean, environmentally friendly and high-yielding for both electron-releasing and electron-withdrawing substituted phenols. The heteropolyacid H 6P2W18O62·24 H2O was employed as catalyst, both bulk and supported on silica. No stoichiometric activation of the carboxyl group or condensing reagents is necessary. The effects of temperature, reaction time, amount of the catalyst used and mole ratio of the reactants on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % mass ratio of catalyst to reactant. Eighteen aryl and phthalimidoethyl cinnamates were obtained, yields ranged in 84-95% for most of the esters. The catalyst shown to be reusable for at least three times without occurring an appreciable loss of its activity.
format Articulo
Articulo
author Ruiz, Diego Manuel
Romanelli, Gustavo Pablo
Bennardi, Daniel Oscar
Baronetti, Graciela Teresita
Thomas, Horacio Jorge
Autino, Juan Carlos
author_facet Ruiz, Diego Manuel
Romanelli, Gustavo Pablo
Bennardi, Daniel Oscar
Baronetti, Graciela Teresita
Thomas, Horacio Jorge
Autino, Juan Carlos
author_sort Ruiz, Diego Manuel
title Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
title_short Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
title_full Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
title_fullStr Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
title_full_unstemmed Direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
title_sort direct esterification of cinnamic acids with phenols and imidoalcohols: a simple, heteropolyacid-catalyzed procedure
publishDate 2008
url http://sedici.unlp.edu.ar/handle/10915/83477
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