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Sustainability 2009, 1(2), 161-186; doi:10.3390/su1020161
Article

Methanetrisulfonic Acid: A Highly Efficient Strongly Acidic Catalyst for Wagner-Meerwein Rearrangement, Friedel-Crafts Alkylation and Acylation Reactions. Examples from Vitamin E Synthesis

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Received: 23 March 2009 / Accepted: 13 April 2009 / Published: 16 April 2009
(This article belongs to the Special Issue Green Chemistry for Environment and Health)
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Abstract

Methanetrisulfonic acid had been prepared for the first time over 140 years ago, but it was used only scarcely in chemical transformations. In the course of our activities dealing with key-steps of industrial syntheses of vitamins, e.g. economically important vitamin E (acetate), we found that methanetrisulfonic acid is an extremely effective catalyst in a variety of reactions. Examples of its applications are Wagner-Meerwein rearrangements, Friedel-Crafts alkylations and ring closures, as well as acylation reactions. Use of this catalyst in truly catalytic amounts (0.04-1.0 mol%) resulted in highly selective transformations and yields over 95%. (Remark by the authors: We are describing only one example each for the various types of reactions. Therefore, it would be more appropriate to write (here and in the Introduction and in the Conclusion sections): “Wagner-Meerwein rearrangement, Friedel-Crafts alkylation and ring closure, as well as acylation reactions”)
Keywords: Acid catalysis; Brønsted acid; tocopherol; vitamin E; Wagner-Meerwein rearrangement; Friedel-Crafts alkylation; acylation Acid catalysis; Brønsted acid; tocopherol; vitamin E; Wagner-Meerwein rearrangement; Friedel-Crafts alkylation; acylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Bonrath, W.; Aquino, F.; Haas, A.; Hoppmann, S.; Netscher, T.; Pace, F.; Pauling, H. Methanetrisulfonic Acid: A Highly Efficient Strongly Acidic Catalyst for Wagner-Meerwein Rearrangement, Friedel-Crafts Alkylation and Acylation Reactions. Examples from Vitamin E Synthesis. Sustainability 2009, 1, 161-186.

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