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The Fries rearrangement of p-tolyl and o-tolyl acetate catalysed by aluminium chloride

✍ Scribed by N. M. Cullinane; B. F. R. Edwards; V. V. Bailey-Wood

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 280 KB
Volume: 79
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19600791112

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✦ Synopsis

Abstract

The rearrangement of p‐tolyl acetate in nitrobenzene solution catalysed by aluminium chloride gives the o‐hydroxyketone only as rearrangement product. o‐Tolyl acetate under the same treatment yields mainly the para‐substituted hydroxyketone together with a small amount only of the ortho‐substituted compound. Both of these rearrangements appear to be intramolecular and the interpretation proposed for the titanium tetrachloride catalysed transformations of these esters may also be applied in the present case.

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