Acetic Acid → HCID 20042539, compound

Participants

Reaction Steps

To a suspension of 3-(2,6-dimethylbenzyloxy)-2-nitropyridine (2.6 g) in a mixture of acetic acid (26 ml), acetic anhydride (39 ml) and sulfuric acid (5 ml) was added chromium trioxide (2.5 g) portionwise during a period of 20 minutss at 10° C. After being stirred for 2 hours at the same temperature the reaction mixture was poured into ice-water and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl alcohol and the solution was made strongly basic to litmus with an aqueous solution of 24% sodium hydroxide with ice-cooling. After being stirred for 2.5 hours at an ambient temperature, the mixture was diluted with ice water. The resulting precipitates were filtrated off and dried to give a mixture (1.29 g) of 3-(2,6-diformylbenzyloxy)-2-nitropyridine and 3-(2-formyl-6-methylbenzyloxy)-2-nitropyridine.

Provenance & Evidence