Water → 4-Iodo-2-nitrobenzoic acid

HRID 2265257Notes

Reaction equation

HRID 2265257 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 acid

Procedure

4-Iodo-2-nitrotoluene (9.0 g, 34.2 mmol), KMnO4 (22.0 g, 139 mmol) and water (340 mL) were heated at reflux for 5 h. The resulting brown suspension was filtered through a pad of diatomaceous earth, washing with water. The basic filtrate was acidified with conc. HCl. The resulting solids were collected by suction filtration and dried to afford 1.86 g of the acid. The mother liquor was extracted with DCM (3×), and the combined extracts were dried (Na2SO4) and concentrated to afford an additional 0.16 g of the benzoic acid. Total yield=2.02 g (20%). 1H NMR (400 MHz, CD3OD): 8.13 (d, J=1.6, 1H), 8.01 (dd, J=8.1, 1.6, 1H), 7.50 (d, J=8.1, 1H).

Workup

  1. temperatureat reflux for 5 h
  2. filtrationThe resulting brown suspension was filtered through a pad of diatomaceous earth
  3. washwashing with water
  4. filtrationThe resulting solids were collected by suction filtration
  5. customdried

Sources & evidence

ORD record
ord-e376598a12ce4456a94f52ce23f39b6a
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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