Copper (II)-β-cyclodextrin aided oxidation of eugenol

Abstract

Oxidation of eugenol [3-(4-hydroxy-3-methoxyphenyl)-prop-1-ene] is carried out in acetic acid with H₂O₂ at room temperature in presence of Cu(II)-β-CD or β-CD or HPβ-CD and CUSO₄. The products are characterized by ¹H NMR. The peracetic acid produced <i>in situ, </i>results in oxidation of phenolic OH to its quinonic form. The olefinic bond remains

unaffected. Although the reaction occurs to a lesser extent in the absence of the copper compound (15.4% in the control reaction, 16.6% in the presence of 1 equivalent β-CD) , higher yields are observed in the presence of CUSO₄ (35.3%) and Cu(II)-β-CD (53.8%). Of the two, Cu(II)-β-CD gives the highest yield indicating that there is a specific orientation of

eugenol phenolic OH group with respect to the copper ion present inside the β-CD cavity.