Nitration of p-cymene. Exchange and rearomatization reactions of p-cymene adducts

Abstract

Nitration of p-cymene in acetic anhydride gives a mixture of cis- and trans-1-isopropyl-4-methyl-4-nitro-1,4-dihydrophenyl acetate as the main product as well as 2- and 3-nitro-p-cymene and p-nitrotoluene. Acid-catalysed methanolysis of the acetoxynitro adduct gives a mixture of the cis- and trans-methoxynitro adducts. Under basic conditions the acetate adduct is converted into the corresponding alcohol which is in turn rearomatized to 2-isopropyl-4-methylphenol. The adducts rearomatize to 2-nitro-p-cymene in strong acid.