Efficient and Convenient Method for Synthesis of Benzofuran-3-acetic Acids and Naphthafuran-acetic Acids

Abstract

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, ¹H NMR, ¹³C 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.

GRAPHICAL ABSTRACT

Keywords:

• Benzofuran
• coumarin
• heterocycles
• Perkin
• transformation

ACKNOWLEDGMENTS

The authors thank the SAIF Indian Institute of Technology Madras, Chennai, for the data collection; Sigma-Aldrich Chemicals Pvt. Ltd., Bangalore, India, for ¹H NMR and ¹³C NMR spectra; and USIC K.U. Dharwad for IR spectral data.

SUPPLEMENTAL MATERIAL

Full experimental details, ¹H and ¹³C NMR spectra, crystallographic information, and other spectral data for this article can be accessed on the publisher’s website.