Acetic Acid → 2'-Hydroxy-5'-nitroacetophenone

Participants

Reaction Conditions

Reaction Steps

2-Hydroxyacetophenone (25.0 g, 183.62 mmol) (B6) was taken up in acetic acid (150 mL) and heated to 35° C. To this solution was then added concentrated nitric acid (26 mL) dropwise over 1.5 hours. After the addition the reaction mixture was stirred overnight at room temperature and worked up by pouring into ice water. The oil so obtained was extracted with ethyl acetate. The ethyl acetate layer was then dried (MgSO4), filtered, concentrated to an oil under reduced pressure and coevaporated with heptane to remove residual acetic acid. The residue was taken up in 50% dichloromethane in heptane and subjected to flash chromatography eluting with the same solvent mixture. The first major band was collected and concentrated to give the desired 2-hydroxy-5-nitroacetophenone, yield 12.0 g (39%). The 2-hydroxy-3-nitroacetophenone isomer was also formed in this reaction and could readily be isolated from the same chromatography column.

Provenance & Evidence