Water → 5-Nitro-2-thenoic acid

HRID 1597322Notes

Reaction equation

HRID 1597322 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.C(Cl)Cl>[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

7

Reactant 4

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

Product 1

HCID 805915-Nitro-2-thenoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

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 excited 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. washThe extract was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give 967 mg (90%) of yellow amorphous

Sources & evidence

ORD record
ord-6c1ea058973341b8a2774cb8779b9813
Source dataset
uspto-grants-2001_09
Patent number
US06294557B1

Reaction notes

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