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12-Tungstophosphoric acid supported on inorganic oxides as heterogeneous and reusable catalysts for the selective preparation of alkoxymethyl ethers and their deprotections under different reaction conditions

  • Iraj Mohammadpoor-Baltork
  • , Majid Moghadam
  • , Shahram Tangestaninejad
  • , Valiollah Mirkhani
  • , Arsalan Mirjafari
  • University of Isfahan

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A wide variety of primary and secondary alcohols were efficiently converted to their corresponding methoxymethyl (MOM) and ethoxymethyl (EOM) ethers in the presence of catalytic amounts of supported H3PW12O40 on silica gel and zirconia at room temperature and under microwave irradiation at solvent-free conditions, whereas, phenols and tertiary alcohols remained intact under the same reaction conditions. Deprotection of these ethers to their parent alcohols was also achieved using these heterogeneous catalysts in ethanol, as a green solvent, under reflux conditions and microwave irradiation. Selective deprotection of primary and secondary MOM- and EOM-ethers in the presence of phenolic and tertiary ones, methyl and benzyl ethers, esters and trimethylsilyl ethers was achieved by these reagent systems. The present methodology offers several advantages such as short reaction times, high yields, simple procedure, heterogeneous reaction conditions, selectivity, non-toxicity and reusability of the catalysts.

Original languageEnglish
Pages (from-to)2612-2624
Number of pages13
JournalPolyhedron
Volume27
Issue number12
DOIs
StatePublished - Aug 21 2008

Keywords

  • 12-Tungstophosphoric acid
  • Alkoxymethylation
  • Microwave irradiation
  • Silica gel
  • Zirconia

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