Acetic Acid → Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

In a 500 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 138.0 of the solution mainly containing methyl 4-(3-chloropropoxy)-3-methoxybenzoate, 0.93 g (13.7 mmol) of sodium nitrite, and 90 mL of acetic acid. The resulting mixture was heated to 40-50° C. under stirring. To the reaction mixture was dropwise added slowly 111.5 g (215.2 mmol) of nitric acid (60 wt. %), and the mixture was kept at the same temperature for 2 hours. After the reaction was complete, 210 mL of water was added to the reaction mixture. Then, the organic portion was separated and washed with 210 mL of warm water. Analysis of the organic portion by high performance liquid chromatography (absolute quantitative analysis) indicated that 78.7 g (reaction yield: 94.5%) of methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate was produced.

Provenance & Evidence