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Clean-chemistry synthesis of 2-tetralones in a single-stage acylation-cycloalkylation process.

Abstract
The preparation of substituted-2-tetralones by direct reaction of a 1-alkene with a substituted phenylacetic acid in a reaction system of trifluoroacetic anhydride (TFAA) and phosphoric acid is described. This single-stage process involves in situ formation of a mixed anhydride of the phenylacetic acid and acylation of the alkene by this species followed by cycloalkylation of the aromatic ring. This is a cleaner approach to the synthesis of 2-tetralones compared to Friedel-Crafts aliphatic acylation-cycloalkylation in that use of thionyl chloride, aluminum trichloride, and a chlorinated hydrocarbon solvent is eliminated. In addition, the atom efficiency is augmented by recovery of the spent TFAA as trifluoroacetic acid (TFA) and conversion of this back to TFAA by dehydration.
AuthorsA D Gray, T P Smyth
JournalThe Journal of organic chemistry (J Org Chem) Vol. 66 Issue 21 Pg. 7113-7 (Oct 19 2001) ISSN: 0022-3263 [Print] United States
PMID11597238 (Publication Type: Journal Article)

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