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Synthesis 1988; 1988(10): 763-766
DOI: 10.1055/s-1988-27701
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Metal Template ortho-Acylation of Phenols. Direct Synthesis of Salicylic Acid Chlorides and Derivatives

Giovanni Sartori* , Giuseppe Casnati, Franca Bigi, Giovanni Bonini
  • *Istituto di Chimica Organica dell'Università, Viale delle Scienze, I-43100 Parma, Italy
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Publication Date:
12 September 2002 (online)

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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.