Chloroacetic Acid → Benzoic acid, 4-(methylsulfonyl)-2-nitro-

Temperature

15 °C

A 100 mL round bottom flask equipped with a reflux condenser, thermometer and magnetic stirrer was charged with 1.9 g (15 mmol) of sodium sulfite, 5.1 g (60 mmol) of sodium bicarbonate and 20 mL of water. The resulting slurry was cooled to 15° C. and 4.0 g (14 mmol) of 2-nitro-4-(chlorosulfonyl)benzoyl chloride was added over 5 minutes. The reaction mixture was stirred at 15° C. for three hours and then at ambient temperature overnight. After warming to 40° C., 3.1 g (27 mmol) of the sodium salt of chloroacetic acid was added to the aqueous solution of 2-nitro-4-sulfinylbenzoic acid and the reaction mixture heated to reflux. After heating for 7 hours, the reaction mixture was allowed to cool to ambient temperature, diluted with 30 mL of water and washed with 50 mL of ethyl acetate. The aqueous layer was acidified with concentrated HCl and extracted with 75 mL of ethyl acetate. The organic solution was concentrated to afford 3.0 g (87% yield) of 2-nitro-4-(methylsulfonyl)benzoic acid as a pale yellow solid.

1. customA 100 mL round bottom flask equipped with a reflux condenser
2. customat ambient temperature
3. customovernight
4. temperatureAfter warming to 40° C.
5. temperaturethe reaction mixture heated to reflux
6. temperatureAfter heating for 7 hours
7. temperatureto cool to ambient temperature
8. washwashed with 50 mL of ethyl acetate
9. extractionextracted with 75 mL of ethyl acetate
10. concentrationThe organic solution was concentrated

ORD record

ord-3033515be1dd471381dfcb1a2ee7ab3a

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05157150