Water → 5-Nitro-2-thenoic acid

HRID 382294Notes

Reaction equation

HRID 382294 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 mxure and extracted with CH2Cl2. The exact 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 exact 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-3956e5b634124e83b85346257cb02765
Source dataset
uspto-grants-2001_10
Patent number
US06310061B2

Reaction notes

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