Acetic Acid → 3-(3-Chloropropoxy)-4-methoxy-6-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

In a 50 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 9.57 g (38.7 mmol) of 3-(3-chloropropoxy)-4-methoxybenzoic acid (purity: 99%) obtained in Reference Example III-13, 0.27 g (3.87 mmol) of sodium nitrite, and 12.5 mL of acetic acid. The resulting mixture was heated to 40° C. under stirring. To the reaction mixture was dropwise added slowly 16.2 g (154.8 mmol) of nitric acid (60 wt. %), and the mixture was heated at the same temperature for 5 hours. After the reaction was complete, 20 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 successively with 30 mL of water and 30 mL of n-heptane, and dried under reduced pressure, to give 10.4 g (isolated yield: 92.0%, purity: 99% in terms of area percentage determined by high performance liquid chromatography) of 4-methoxy-5-(3-chloropropoxy)-2-nitrobenzoic acid as a white crystalline product. 4-Methoxy-5-(3-chloropropoxy)-2-nitrobenzoic acid had the following characteristics.

Provenance & Evidence