Tetrahedron

Unusual Friedel-Crafts reactions, IX. One-step ortho-acylation of phenols with α, β-unsaturated acyl chlorides. Synthesis of 2'-hydroxychalcones and sorbicillin …

F Bigi, G Casiraghi, G Casnati, S Marchesi, G Sartori…

Index: Bigi, Franca; Casiraghi, Giovanni; Casnati, Giuseppe; Marchesi, Stefania; Sartori, Giovanni; Vignali, Carlo Tetrahedron, 1984 , vol. 40, # 20 p. 4081 - 4084

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Citation Number: 16

Abstract

The reaction of bromomagnesium phenolates 1 in toluene with α, β-unsaturated acyl chlorides 2 at room temperature provides a straightforward highly selective synthesis of α, β- unsaturated 2-hydroxyarylketones 3. 2'-Hydroxychalcones, ortho-sorbylphenols including sorbicillin 3g, and ortho-propiolylphenols were usefully synthesized by this way. This reaction provides a further example of the synthetic versatility of the chelation-controlled ...