Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes

Ram S. Mohan, Neil J. Baldwin, Anna N. Nord, Brendan D. O’Donnell

Research output: Journal ArticleArticlepeer-review

Abstract

Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.
Original languageAmerican English
JournalTetrahedron Letters
Volume53
StatePublished - 2012

Keywords

  • Iron and its compounds
  • Acylation
  • Alcohols
  • Diols
  • Esters
  • Green chemistry
  • Phenols

Disciplines

  • Organic Chemistry

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