Water → 4-Iodo-2-nitrobenzoic acid

HRID 1892159Notes

Reaction equation

HRID 1892159 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[O-:12][Mn](=O)(=O)=O.[K+].[OH2:18]>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:12])=[O:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 1704814-Iodo-2-nitrotolueneHCID 516875Potassium Permanganate

Product 1

HCID 189198834-Iodo-2-nitrobenzoic acidYield 20%

Procedure

To a mixture of 4-iodo-2-nitrotoluene (9.0 g, 34 mmol) in H2O (340 mL) was added KMnO4 (22.0 g, 139 mmol). The mixture was heated at reflux for 5 h and then cooled to rt and filtered through Celite®. The filtrate was acidified to pH=2 with conc. HCl. The precipitate that formed and was filtered and dried to give 4-iodo-2-nitrobenzoic acid (2.0 g, 20%). The filtrate was extracted with DCM (3×200 mL). The organic solutions were combined, dried over Na2SO4, filtered, and concentrated to provide a second lot of 4-iodo-2-nitrobenzoic acid (0.18 g, 2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h
  3. filtrationfiltered through Celite®
  4. customThe precipitate that formed
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-e5d5f4f1acf44b2f9ae97a9f1a2e7b3a
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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