Water → 5-Nitro-2-thenoic acid

HRID 428584Notes

Reaction equation

HRID 428584 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 1 H, 30 ml of isopropanol was added to the mixture. H2O was added to the mature and extracted with CH2Cl2. The extra 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 extra 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-dcac0103fef846c89f0963f4f0398ddc
Source dataset
uspto-grants-2001_11
Patent number
US06313302B2

Reaction notes

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