96249-84-2Relevant academic research and scientific papers
Metal Template ortho-Acylation of Phenols. Direct Synthesis of Salicylic Acid Chlorides and Derivatives
Sartori, Giovanni,Casnati, Giuseppe,Bigi, Franca,Bonini, Giovanni
, p. 763 - 766 (1988)
A direct synthesis of salicylic acid chlorides is achieved via "metal-driven" intracomplex acylation of bromomagnesium and aluminum phenoxides with phosgene.Salicylic acids 5 and some derivatives 6, 7 can be obtained by quenching the reaction mixture with convenient reagents.Moreover the reaction of lithium phenylacetylide with 3 provides a new convenient approach to ortho-hydroxyaryl alkynyl ketones like 8.The oriented complex 2, involving the metal phenoxide and phosgene is proposed to account for the ortho-regioselective control of the reaction.
UNUSUAL FRIEDEL-CRAFTS REACTIONS, IX. ONE-STEP ORTHO-ACYLATION OF PHENOLS WITH α,β-UNSATURATED ACYL CHLORIDES. SYNTHESIS OF 2'-HYDROXYCHALCONES AND SORBICILLIN ANALOGUES
Bigi, Franca,Casiraghi, Giovanni,Casnati, Giuseppe,Marchesi, Stefania,Sartori, Giovanni,Vignali, Carlo
, p. 4081 - 4084 (2007/10/02)
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.
