Hydrochloric Acid → 2-Iodo-4,5-dimethoxybenzoic acid

HRID 2175711Notes

Reaction equation

HRID 2175711 reaction equation
[I:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].[O-:14][Mn](=O)(=O)=O.[K+].Cl>CC#N.O>[I:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[C:4]([OH:14])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516875Potassium PermanganateHCID 110117632-Iodo-4,5-dimethoxybenzaldehyde

Product 1

HCID 27584222-Iodo-4,5-dimethoxybenzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-iodo-4,5-dimethoxybenzaldehyde (1.0 g, 3.42 mmol) in CH3CN (25 mL) was added a solution of KMnO4 (0.76 g, 4.79 mmol) in water (15 mL) dropwise at 0° C. The resulting mixture was stirred at room temperature overnight. After the reaction was complete, the pH was adjusted to <7 with 1N HCl. The mixture was extracted with DCM and the organic layers combined, washed with brine, dried over sodium sulfate, and evaporated to give 2-Iodo-4,5-dimethoxybenzoic acid (0.89 g, 85%).

Workup

  1. extractionThe mixture was extracted with DCM
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f5eede36a2e54375b1d29ac54579d374
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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