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Conversion of 2-Alkylcinnamaldehydes to 2-Alkylindanones via a Catalytic Intramolecular Friedel−Crafts Reaction
journal contribution
posted on 2007-08-31, 00:00 authored by Gary B. Womack, John G. Angeles, Vincent E. Fanelli, Christie A. HeyerThe preparation of indanones by the intramolecular acylation
of 3-arylpropanoic acids or halides requires the use of noncatalytic acid promoters. In the presence of 5−10 mol %
FeCl3, in situ generated dimethyl acetals of (E)-2-alkylcinnamaldehydes cyclize to 1-methoxy-2-alkyl-1H-indenes in
good-to-high yields. The 1-methoxyindenes were converted
in high yield into 2-alkylindanones by treatment with
triethylamine, to effect isomerization to the isomeric enol
ethers, followed by acid-catalyzed hydrolysis. Thus, a
catalytic, intramolecular Friedel−Crafts reaction leading to
2-alkylindanones from 2-alkylcinnamaldehydes was developed.
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alkylindanoneCatalyticpresencecyclizeyieldarylpropanoicFeClmethoxyindenepreparationconversionhalidesnoncatalytic acid promotersAlkylcinnamaldehydeisomeric enol etherseffect isomerizationmethoxydimethyl acetalstriethylaminealkylcinnamaldehydehydrolysisFriedelindanoneReactionTheAlkylindanoneintramolecular acylationIntramolecular
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