Synthetic Communications p. 2685 - 2698 (2006)
Update date:2022-08-02
Topics:
Wang, Yang
Wu, Jiang
Xia, Peng
The synthesis of 1,1-dimethyl-4-indanols (3a,b) has been achieved by intramolecular Friedel-Crafts cyclization of 2-(3-methyl-2-butenyl)phenols (5a,b) or 1-methoxy-2-(3-methyl-2-butenyl)benzenes (6a,b) followed by demethylation, respectively. It was found that the solvent was critical for the formation of different products in the intramolecular Friedel-Crafts reactions of 6. The unexpected product 4-methoxy-1,1,6,6-tetramethyl-as-hydrindacene (11) was obtained from the Friedel-Crafts reactions of 6a and its structure was confirmed by X-ray diffraction analysis. The key intermediates 5a,b were prepared by ortho-alkenylation of phenols with 1-bromo-3-methyl-2-butene, and the reaction temperature exerted an obvious impact on the yield of 2-(3-methyl-2-butenyl)phenol (5a). Copyright Taylor & Francis Group, LLC.
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