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

In a 50 mL volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed 10.1 g (36.7 mmol) of methyl 4-(4-chlorobutoxy)-3-methoxybenzoate (purity: 98%) obtained in Reference Example III-9, 0.25 g (3.67 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 115.4 g (146.8 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 10.9 g (isolated yield: 92.0%, purity: 99% in terms of area percentage determined by high performance liquid chromatography) of methyl 5-methoxy-4-(4-chlorobutoxy)-2-nitrobenzoate as a white crystalline product.

1. customIn a 50 mL volume glass flask equipped with a stirrer
2. temperaturethe mixture was heated at the same temperature for 5 hours
3. temperaturethe aqueous mixture was cooled to 20° C.
4. customprecipitating a crystalline product
5. filtrationThe crystalline product was collected by filtration
6. washwashed successively with 30 mL of water and 30 mL of n-heptane
7. customdried under reduced pressure

ORDレコード

ord-8f8e1184feb843de9868d32a1d44770c

出典データセット

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08367824B2