UNUSUAL FRIEDEL-CRAFTS REACTIONS, IX. ONE-STEP ORTHO-ACYLATION OF PHENOLS WITH α,β-UNSATURATED ACYL CHLORIDES. SYNTHESIS OF 2'-HYDROXYCHALCONES AND SORBICILLIN ANALOGUES

Article abstract of DOI:10.1016/0040-4020(84)85088-7

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 approach in the elaboration of phenol derivatives.