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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 3
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Original Articles

Simple and efficient synthesis of benzofuran derivatives from tyrosol

Paolo BovicelliC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, ItalyCorrespondence[email protected]
,
Fabrizio BottaroC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, Italy
,
Carla SappinoC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, Italy
,
Michela TomeiC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, Italy
,
Valentina NardiC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, Italy
,
Ilaria Proietti SilvestriC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, Italy
,
Beatrice MacchiDepartment of System Medicine, “Tor Vergata” University, Rome, Italy
,
Caterina FrezzaDepartment of System Medicine, “Tor Vergata” University, Rome, Italy
&
Giuliana RighiC.N.R. Institute of Biology and Molecular Pathologies (IBPM), Department of Chemistry, Sapienza University of Rome, Rome, Italy
 show all
Pages 242-248 | Received 02 Oct 2015, Published online: 06 Feb 2016
 
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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.

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