The use of environmentally benign Montmorillonite clay in the synthesis of several o-prenylated phenols (1) and 2,2-dimethylbenzopyrans (2) is described. The target pharmacophores, which are present in a broad range of physiologically active natural products, can be generated in good yields via two different clay-catalyzed reactions. Intramolecular [1,3] shift of the corresponding allyl phenyl ethers gives o-prenylated phenols 1. Intermolecular alkylation of substituted phenols with prenyl bromide gives 2,2-dimethylbenzopyrans 2.

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