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A new method for the synthesis of substituted 3-alkyl-3,4-dihydroisocoumarins is described. o-(Oxiranylmethyl)benzonitriles, prepared from isovanillin in five steps, when reacted with nucleophiles such as sodium borohydride or phenylmagnesium chloride/CuI, undergo an intramolecular cyclization to yield the target compounds in good yields, in one pot.

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Reaction of o-(oxiranylmethyl)benzonitriles with sodium borohydride or Grignard reagent/CuI: a new synthesis of substituted 3-alkyl-3,4-dihydroisocoumarins