Selwyn Yorke - An investigation into the unusual formation of an isocoumarin by acylation of 2,3,6-trimethoxytoluene with (E)-2-methylbut-2-enoic acid and trifluoroacetic anhydride

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  Publication Details (including relevant citation   information):

  Journal of the Chemical Society, Perkin Transactions 1:    Organic and Bio-Organic Chemistry (1972-1999) (1991), (1), 89-95


  Prolonged reaction of 2,3,6-(MeO)3C2H2Me with an excess of   premixed (E)-MeCH:CMeCO2H and (CF3CO)2O in air affords   5,6,8-trimethoxy-3,4,7-trimethylisocoumarin (I) in 66% yield as   the sole product isolated, the structure of which was confirmed   by x-ray crystallog.  Shorter reaction times afford products   which enable the identification of the reaction mechanism.

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