Acetic Acid → Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

In a 50 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 1.02 g (4.08 mmol) of methyl 4-(2-chloroethoxy)-3-methoxybenzoate (purity: 98%) obtained in Reference Example III-1, 0.03 g (0.40 mmol) of sodium nitrite, and 1.25 mL of acetic acid. The resulting mixture was heated to 40° C. under stirring. To the reaction mixture was dropwise added slowly 1.72 g (16.5 mmol) of nitric acid (60 wt. %), and the mixture was heated to the same temperature for 5 hours. After the reaction was complete, 5 mL of water was added to the reaction mixture, and the aqueous mixture was cooled to 20° C., precipitating a crystalline product. The crystalline product was collected by filtration, washed with 5 mL of water, and dried under reduced pressure, to give 1.12 g (isolated yield: 93.0%, purity: 98% in terms of area percentage determined by high performance liquid chromatography) of methyl 5-methoxy-4-(2-chloroethoxy)-2-nitrobenzoate as a white crystalline product.

Provenance & Evidence