Nitric Acid → Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

Nitric Acid (18 mL) was added dropwise to a solution of 15.0 g (77.3 mmol) of 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester in 45 mL of HOAc. The solution was heated at 60° C. for 1.5 h. An additional 9 mL of HNO3 was then added and heating was continued for 1.5 h at 70° C. The reaction was poured into ice-H2O and the solid product was collected, washed well with H2O and dried. Recrystallization from heptane-toluene yielded 16.8 g of the title compound as yellow crystals: mass spectrum (electron impact, m/e): 239.

Provenance & Evidence