title: Synthesis of o-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone.
abstract: A simple procedure for the synthesis of a variety of o-carboxyarylacrylic acids has been developed with Oxone (2KHSO5·KHSO4·K2SO4); the oxidation reaction involves the stirring of methoxy/hydroxy-substituted naphthalenes, phenanthrenes, anthracenes, etc. with Oxone in an acetonitrile-water mixture (1:1, v/v) at rt. Mechanistically, the reaction proceeds via initial oxidation of naphthalene to o-quinone, which undergoes cleavage to the corresponding o-carboxyarylacrylic acid. The higher aromatics are found to yield carboxymethyl lactones derived from the initially formed o-carboxyarylacrylic acids.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, INDIA.
authors.forename: Keshaba Nanda
authors.initials: KN
authors.lastname: Parida
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, INDIA.
authors.forename: Jarugu Narasimha
authors.initials: JN
authors.lastname: Moorthy