Herein, we report an efficient and convenient method for synthesis of benzofuran-3-acetic acids and naphthafuran-acetic acids 5a-p by the reaction of substituted-4-bromomethylcoumarins with aqueous sodium hydroxide at refluxing temperature. The obtained products are characterized by infrared, 1 H NMR, 13 C NMR, and mass spectral data. Structures 5a and 5e are confirmed by their single x-ray diffraction studies. The advantages of this method are good yields, easy workup, and no chromatographic purifications.
Acids. -The base-catalyzed Perkin rearrangement of coumarins of type (I) affords the corresponding benzofuran derivatives (II). -(BASANAGOUDA*, M.; NARAYANACHAR; MAJATI, I. B.; MULIMANI, S. S.; SUNNAL, S. B.; NADIGER, R. V.; GHANTI, A. S.; GUDAGERI, S. F.; NAIK, R.; NAYAK, A.; Synth. Commun. 45 (2015) 19, 2195-2202, http://dx.
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