Green Methodology Development for the Surfactant Assisted Williamson Synthesis of 4-Benzyloxy Benzoic Acid (Ether) in Aqueous Media

Sangita Mandal; Satyajit Biswas; Monohar Hossain Mondal; Bidyut Saha

doi:10.3139/113.110676

Artikel

Green Methodology Development for the Surfactant Assisted Williamson Synthesis of 4-Benzyloxy Benzoic Acid (Ether) in Aqueous Media

Sangita Mandal , Satyajit Biswas , Monohar Hossain Mondal und Bidyut Saha

Veröffentlicht/Copyright: 9. März 2020

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Aus der Zeitschrift Tenside Surfactants Detergents Band 57 Heft 2

Abstract

Modern science and technology promote synthesis routes which are eco-friendly, chemicals which are promoted as “green” and solvents which are less toxic. A convenient method for the synthesis of ether by the reaction of 4-hydroxy benzoic acid and benzyl chloride using a surfactant as catalyst has been developed. The targeted ether is completely immiscible in water but in association with the interface active surfactants, the production of such a hydrophobic organic compound in water has been made possible. Micelles produce a pseudo-cellular organic environment to isolate species from the bulk solvent and favour the compartmentalization of reagents as well. Thus, the enhancement of the local concentration takes place and consequently the reactivity increases. The interaction of such unique chemo-, regio- and stereo-selectivity of surfactants made this reaction feasible. Organic species added to a micellar media are distributed between bulk water and micelles depending on their polarity, charge and dimension. This novel chemistry describes a set of green methods for carrying out this new generation Williamson reaction which can also be used for selective O-alkylation.

Kurzfassung

Moderne Wissenschaft und Technologie fördern umweltfreundliche Synthesewege, umweltfreundliche Chemikalien und gering toxische Lösungsmittel. Es wurde ein geeignetes Verfahren zur Synthese von Ether durch Umsetzung von 4-Hydroxybenzoesäure und Benzylchlorid unter Verwendung von Tensid als Katalysator entwickelt. Das Zielprodukt Ether ist in Wasser nicht vollständig mischbar, doch in Verbindung mit den grenzflächenaktiven Tensiden konnte eine solche hydrophobe organische Verbindung in Wasser hergestellt werden. Mizellen produzieren eine pseudozelluläre organische Umgebung, um Spezies aus dem Bulklösungsmittel zu isolieren und die Kompartimentierung von Reagenzien zu begünstigen. Dadurch wird die lokale Konzentration erhöht und die Reaktivität nimmt folglich zu. Diese Reaktion wird durch das einzigartige Zusammenspiel der Chemo-, Regio- und Stereoselektivität von Tensiden ermöglicht. Organische Spezies, die mizellaren Medien zugesetzt werden, verteilen sich je nach Polarität, Ladung und Dimension zwischen dem Bulkwasser und den Mizellen. Diese neue Chemie beschreibt eine Reihe umweltfreundlicher (grüner) Methoden zur Durchführung der Williamson-Reaktion der neuen Generation, die auch für die selektive O-Alkylierung verwendet werden kann.

Key words: Williamson reaction; micellar catalysis; green chemistry; ether production

Stichwörter: Williamson-Reaktion; mizellare Katalyse; grüne Chemie; Etherproduktion

∗ Correspondence address, Prof. Dr. Bidyut Saha, Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Burdwan 713104, WB, India, Mobile: +919476341691, Tel.: +91-342-2533913 (O), Fax: +91-342-2530452 (O), E-Mail: b_saha31@rediffmail.com

Sangita Mandal was born in Khatra, Bankura in 1991. She passed her M.Sc degree from The University of Burdwan in 2013 and got UGC-RGNF fellowship on the year 2015. She also clears the NET exam in Chemical Sciences in 2012. She is working in lab in “Homogeneous Catalysis” division.

Satyajit Biswas was born in Hooghly in 1980. He passed his M.Sc degree from The University of Burdwan in 2003. He is working in Department of Chemistry, Hooghly Women's College, and Hooghly as a Professor and also working as a part-time fellow in lab in “Homogeneous Catalysis” division.

Monohar Hossain Mondal was born in kalna, Burdwan in 1991. He has completed his M.Sc. degree from The University of Burdwan in 2013 and received UGC-NET JRF in the same year. After completing one year as JRF at the Bioremediation Laboratory (The University of Burdwan), he has been appointed as WBES Officer by the Government of West Bengal and presently working as Assistant Professor in Chem- istry at Govt. General Degree College at Singur, Hooghly, WB, India.

Bidyut Saha was born in Birbhum, WB, India in 1975. He obtained his Ph.D degree from Visva Bharati University, India in 2007. He was a visiting scientist for the year 2009–2010 in the Department of Chemistry, UBC, Vancouver, Canada. Dr. Saha is presently working as Professor in the Department of Chemistry, The University of Burdwan, India. His area of interests is bioremediation of toxic metal, micellar catalysis and chemical kinetics. He has already published more than 110 papers in international journals.

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Received: 2019-05-30

Accepted: 2019-10-28

Published Online: 2020-03-09

Published in Print: 2020-03-16

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Artikel in diesem Heft

https://doi.org/10.3139/113.110676

Schlagwörter für diesen Artikel

Williamson reaction; micellar catalysis; green chemistry; ether production