Synthesis of 2-(Prop-2-ynyloxy) Benzaldehyde using Salicyl Aldehyde and Propargyl Bromide in Aqueous Micellar Media

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

doi:10.3139/113.110629

Article

Synthesis of 2-(Prop-2-ynyloxy) Benzaldehyde using Salicyl Aldehyde and Propargyl Bromide in Aqueous Micellar Media

Sangita Mandal , Swagata Mandal , Satyajit Biswas , Monohar Hossain Mondal and Bidyut Saha

Published/Copyright: July 13, 2019

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From the journal Tenside Surfactants Detergents Volume 56 Issue 4

Abstract

Advances in science and technology are promoting eco-friendly synthesis routes, green chemicals, and non-hazardous solvents. A suitable method for the synthesis of 2-(prop-2-ynyloxy) benzaldehyde was developed using three different aqueous micellar media. The targeted product ether is completely immiscible in water, but in combination with interface active surfactants it has been possible to produce the hydrophobic organic compound in water. Micelles function as a pseudocellular organic environment to isolate species from the main solvent and favor compartmentalization of reagents. There is an increase in the local concentration and consequently the reactivity increases. The use of such unique chemo-, regio-, and stereoselectivity renders this reaction new. Organic species added to a micellar media are distributed between water and micelles depending on polarity, charge, and size. In the experiments it was observed that salicylaldehyde and propargyl bromide interacted best in CTAB media and the yield of the formed product was 96 %.

Kurzfassung

Fortschritte in Wissenschaft und Technologie fördern umweltfreundliche Synthesewege, grüne Chemikalien und nicht gefährliche Lösungsmittel. Ein geeignetes Verfahren zur Synthese von 2-(Prop-2-inyloxy)benzaldehyd wurde unter Verwendung von drei verschiedenen wässrigen mizellaren Medien entwickelt. Das angestrebte Ether-Produkt ist mit Wasser nicht mischbar, aber in Verbindung mit den grenzflächenaktiven Tensiden wurde die Herstellung der hydrophoben organischen Verbindung in Wasser ermöglicht. Mizellen fungieren als pseudozellige organische Umgebung, um Spezies aus dem Hauptlösungsmittel zu isolieren und die Kompartimentierung von Reagenzien zu begünstigen. Es kommt zu einer Erhöhung der lokalen Konzentration und folglich steigt die Reaktivität. Die Verwendung einer solchen einzigartigen Chemo-, Regio- und Stereoselektivität ist neu für diesen Reaktionstyp. Organische Spezies, die zu mizellaren Medien hinzugefügt werden, werden je nach Polarität, Ladung und Größe zwischen Wasser und Mizellen verteilt. Bei den Experimenten wurde beobachtet, dass Salicylaldehyd und Propargylbromid in CTAB-Medien am besten zusammenwirkten und das Produkt mit einer Ausbeute von 96 % gebildet wurde.

Key words: 2-(prop-2-ynyloxy) benzaldehyde; salicylaldehyde; propargyl bromide and micellar catalysis

Stichwörter: 2-(Prop-2-inyloxy)benzaldehyd; Salicylaldehyd; Propargylbromid; mizellare Katalyse

∗Correspondence address, Prof. Dr. B. Saha, Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Burdwan-713104, WB, India, 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.

Swagata Mandal was born in 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 is working in my 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, Hooghly as a Professor and also working as a part-time fellow in lab in “Homogeneous Catalysis” division.

Dr. Monohar Hossain Mondal was born in Burdwan. He passed his M.Sc degree from The University of Burdwan in 2013. He obtained his Ph.D degree from Burdwan University, India in 2017. His area of interests is bioremediation of toxic metal, micellar catalysis and chemical kinetics. He has already published more than 12 papers in international journals.

Dr. 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: 2018-10-31

Accepted: 2019-01-04

Published Online: 2019-07-13

Published in Print: 2019-07-17

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https://doi.org/10.3139/113.110629

Keywords for this article

2-(prop-2-ynyloxy) benzaldehyde; salicylaldehyde; propargyl bromide and micellar catalysis