Nitric Acid → 5-Acetyl-3-nitrosalicylic acid

Participants

Reaction Conditions

Reaction Steps

5-Acetylsalicylic acid (9.0 g) was dissolved in concentrated sulphuric acid (20 ml). The solution was cooled to 0° C. and treated, with stirring, with a mixture of concentrated nitric acid (density 1.42; 3.8 ml) and concentrated sulphuric acid (3.8 ml), dropwise, at such a rate that the temperature did not exceed 5° C. The mixture was left to stand at 0° C. for 5 hours and then it was poured onto a mixture of ice and water (100 ml). The precipitated solid was filtered off and recrystallized from water to give 5-acetyl-3-nitrosalicylic acid (8.6 g), m.p. 192°-193° C.

Provenance & Evidence