Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid

Thenkrishnan Kumaraguru; Avala Vedamayee Devi; Vidavalur Siddaiah; Kishor Rajdeo; Nitin W. Fadnavis

doi:10.1016/j.apcata.2014.08.026

Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid

Thenkrishnan Kumaraguru, Avala Vedamayee Devi, Vidavalur Siddaiah, Kishor Rajdeo, Nitin W. Fadnavis

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

12-Phosphotungstic acid supported on silica gel, zirconium sulfate, and a combination of silica gel and zirconium sulfate (50% w/w) were employed as solid acid catalysts for regioselective acylation of 2-methoxynaphtalene with acetic anhydride. 1-(6-Methoxynaphthalen-2-yl)ethanone (2,6-AMN), a commercially important intermediate for production of Naproxen, was obtained with excellent selectivity (>98%) at 67-68% conversion using 12-phosphotungstic acid supported on silica gel 20% (w/w) in refluxing tetrachloroethane. The unreacted starting material can be easily separated from the product by a simple crystallization from nonane.

Original language	English (US)
Pages (from-to)	55-61
Number of pages	7
Journal	Applied Catalysis A: General
Volume	486
DOIs	https://doi.org/10.1016/j.apcata.2014.08.026
State	Published - Sep 22 2014

Bibliographical note

Funding Information:
We thank CSIR New Delhi for financial support under XII 5 year plan CSC0108-ORIGIN, and Prof. Dr V Vishwanathan, Sreyas Institute of Engineering and Technology, Hyderabad for helpful discussions.

Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.

Keywords

Acylation
Naproxen
Phosphotungstic acid
Silica gel
Supported
Zirconium sulfate

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10.1016/j.apcata.2014.08.026

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title = "Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid",

abstract = "12-Phosphotungstic acid supported on silica gel, zirconium sulfate, and a combination of silica gel and zirconium sulfate (50% w/w) were employed as solid acid catalysts for regioselective acylation of 2-methoxynaphtalene with acetic anhydride. 1-(6-Methoxynaphthalen-2-yl)ethanone (2,6-AMN), a commercially important intermediate for production of Naproxen, was obtained with excellent selectivity (>98%) at 67-68% conversion using 12-phosphotungstic acid supported on silica gel 20% (w/w) in refluxing tetrachloroethane. The unreacted starting material can be easily separated from the product by a simple crystallization from nonane.",

keywords = "Acylation, Naproxen, Phosphotungstic acid, Silica gel, Supported, Zirconium sulfate",

author = "Thenkrishnan Kumaraguru and Devi, {Avala Vedamayee} and Vidavalur Siddaiah and Kishor Rajdeo and Fadnavis, {Nitin W.}",

note = "Funding Information: We thank CSIR New Delhi for financial support under XII 5 year plan CSC0108-ORIGIN, and Prof. Dr V Vishwanathan, Sreyas Institute of Engineering and Technology, Hyderabad for helpful discussions. Publisher Copyright: {\textcopyright} 2014 Elsevier B.V. All rights reserved.",

year = "2014",

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doi = "10.1016/j.apcata.2014.08.026",

language = "English (US)",

volume = "486",

pages = "55--61",

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T1 - Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid

AU - Kumaraguru, Thenkrishnan

AU - Devi, Avala Vedamayee

AU - Siddaiah, Vidavalur

AU - Rajdeo, Kishor

AU - Fadnavis, Nitin W.

N1 - Funding Information: We thank CSIR New Delhi for financial support under XII 5 year plan CSC0108-ORIGIN, and Prof. Dr V Vishwanathan, Sreyas Institute of Engineering and Technology, Hyderabad for helpful discussions. Publisher Copyright: © 2014 Elsevier B.V. All rights reserved.

PY - 2014/9/22

Y1 - 2014/9/22

N2 - 12-Phosphotungstic acid supported on silica gel, zirconium sulfate, and a combination of silica gel and zirconium sulfate (50% w/w) were employed as solid acid catalysts for regioselective acylation of 2-methoxynaphtalene with acetic anhydride. 1-(6-Methoxynaphthalen-2-yl)ethanone (2,6-AMN), a commercially important intermediate for production of Naproxen, was obtained with excellent selectivity (>98%) at 67-68% conversion using 12-phosphotungstic acid supported on silica gel 20% (w/w) in refluxing tetrachloroethane. The unreacted starting material can be easily separated from the product by a simple crystallization from nonane.

AB - 12-Phosphotungstic acid supported on silica gel, zirconium sulfate, and a combination of silica gel and zirconium sulfate (50% w/w) were employed as solid acid catalysts for regioselective acylation of 2-methoxynaphtalene with acetic anhydride. 1-(6-Methoxynaphthalen-2-yl)ethanone (2,6-AMN), a commercially important intermediate for production of Naproxen, was obtained with excellent selectivity (>98%) at 67-68% conversion using 12-phosphotungstic acid supported on silica gel 20% (w/w) in refluxing tetrachloroethane. The unreacted starting material can be easily separated from the product by a simple crystallization from nonane.

KW - Acylation

KW - Naproxen

KW - Phosphotungstic acid

KW - Silica gel

KW - Supported

KW - Zirconium sulfate

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DO - 10.1016/j.apcata.2014.08.026

M3 - Article

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JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

ER -

Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid

Abstract

Bibliographical note

Keywords

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