Hydrochloric Acid → 5-Nitro-2-thenoic acid

To a 500 mL round bottomed flask with a stirring bar, was added 5-nitrothiophene-2-carboxaldehyde (7.86 g, 50.00 mmol) in CH13CN (50 mL), NaH2PO4 (1.86 g, 13.50 mmol) in water (20 mL), and 30% H2O2 (aq) (6 mL). To this mixture, cooled in an ice bath, was added NaClO2 (8 g, 70.80 mmol) in water (70 mL) dropwise over a period of an hour. The reaction was stirred at room temperature for 5 hours. It was worked up by addition of Na2SO3 (500 mg), acidified with 1M HCl, and then extracted with ethyl acetate (3×). The combined organic layers were washed with water (1×), and brine (1×). Drying (MgSO4), filtration and removal of the solvents in vacuo yielded 5-Nitrothiophene-2-carboxylic acid as a yellow powder.

1. temperatureTo this mixture, cooled in an ice bath
2. extractionextracted with ethyl acetate (3×)
3. washThe combined organic layers were washed with water (1×), and brine (1×)
4. customDrying
5. filtration(MgSO4), filtration and removal of the solvents in vacuo

ORD record

ord-2322554198774954a11b35d46a6b8e62

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05854245