The product obtained when acetophenones are heated with nitric acid in the presence of acetic anhydride varies depending on the substituent on the aromatic ring. Acetophenone and most substituted acetophenones generate symmetrically substituted 3,4-dibenzoyloxadiazole-2-oxides (dibenzoylfuroxans). However, hydroxy-substituted acetophenones undergo ring substitution under these same conditions. Nitration of 2’-hydroxyacetophenone with nitric acid, yields a mixture of 2’-hydroxy-3’-nitro- and 2’-hydroxy-5’-nitroacetophenone, whereas nitration of the 3’-hydroxyacetophenone yields several nitration products. Curiously, the reaction with the 4’-hydroxyacetophenone yields 2,4-dinitrophenol. The products obtained from each reaction were analyzed by NMR spectroscopy and GC-MS.

Comparing the reaction pathways of acetophenones in nitration reactions

ACS Spring Meeting 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.