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

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

Research output: Contribution to journalArticlepeer-review

8 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 languageEnglish (US)
Pages (from-to)55-61
Number of pages7
JournalApplied Catalysis A: General
Volume486
DOIs
StatePublished - 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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