Simple and efficient synthesis of benzofuran derivatives from tyrosol. Issue 3 (1st February 2016)

• Record Type: Journal Article
• Authors: Bovicelli, Paolo; Bottaro, Fabrizio; Sappino, Carla; Tomei, Michela; Nardi, Valentina; Proietti Silvestri, Ilaria; Macchi, Beatrice; Frezza, Caterina; Righi, Giuliana
• Is Part Of: Synthetic communications. Volume 46:Issue 3(2016)
• Page Start: 242
• Page End: 248
• Publication Date: 2016-02-01
• Subjects: Antioxidants -- benzofurans -- heterocyclization -- polyphenols; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2015.1133828
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: A convenient strategy for the preparation of compounds bearing the benzofuran skeleton starting from tyrosol, a phenol largely present in olive oil production waste, with no biological importance, is reported. A bromination/methoxylation sequence, already described for the synthetic transformation of naturally occurring compounds, was exploited. Depending on the solvent used for the methoxylation reaction together with the presence of a 4-phenol moiety respect to the side chain, benzodihydrofurans or a benzofurans derivative can be obtained. GRAPHICAL ABSTRACT: