Water → 5-Nitro-2-thenoic acid

HRID 380355Notes

Reaction equation

HRID 380355 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-thiopenecarboxaidehyde (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. customdried (Na2So4)
  5. concentrationconcentrated
  6. customto give 967 mg (90%) of yellow amorphous

Sources & evidence

ORD record
ord-faeaefd161bb4953b7a6c4b9e3ba5300
Source dataset
uspto-grants-2001_10
Patent number
US06303602B1

Reaction notes

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