Water → 5-Nitro-2-thenoic acid

HRID 1597388Notes

Reaction equation

HRID 1597388 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(C)=[O:13].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.O>CC(C)=O>[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:13])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 131709961Jones' reagent

Product 1

HCID 805915-Nitro-2-thenoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-nitro-2-thiophenecarboxaldehyde (1.00 g, 6.24 mmol) in acetone (50 ml) was added Jones reagent (8N in acetone, 8.12 ml, 65 mmol) at −20° C. After stirring for 1H 30 ml of isopropanol was added to the mixture. H2O was added to the mixture and extracted with CH2Cl2. The extract was washed with water, brine, dried (Na2SO4), and concentrated to give 967 mg (90%) of yellow amorphous.

Workup

  1. additionwas added to the mixture
  2. extractionextracted with CH2Cl2
  3. washThe extract was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give 967 mg (90%) of yellow amorphous

Sources & evidence

ORD record
ord-f8a20168740b4f1b8f50c121f082f46e
Source dataset
uspto-grants-2001_09
Patent number
US06294569B2

Reaction notes

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