Hydrochloric Acid → 2-Iodo-3-methoxybenzoic acid

HRID 859121Notes

Reaction equation

HRID 859121 reaction equation
[CH3:1][O:2][C:3]1[C:4](NC(=O)C(C)(C)C)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].Cl.N([O-])=O.[Na+].[I-:24].[K+]>O>[I:24][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 13894021HCID 13894021, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 4582192-Iodo-3-methoxybenzoic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 3-methoxy-2-pivalamidobenzoic acid (20 g, 0.08 mol) and 7M hydrochloric acid (280 ml) was heated under reflux for 2 hours then cooled to 0° C. A solution of sodium nitrite (5.8 g, 0.09 mol) in water (46 ml) was added dropwise at <5° C., the mixture was stirred at 0–5° C. for 2 hours, then a solution of potassium iodide (17.8 g, 0.11 mol) in water (39 ml) was added dropwise at 0–5° C. The stirred mixture was heated at 70–80° C. for 2 hours then cooled in ice. The product was extracted into ethyl acetate (3×300 ml), the combined extracts were washed with 20% aqueous sodium thiosulphate solution (3×300 ml), then they were dried (MgSO4) and the solvent was removed in vacuo to leave 2-iodo-3-methoxybenzoic acid (13 g, 58%) as a solid, m.pt. 142–146° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe stirred mixture was heated at 70–80° C. for 2 hours
  4. temperaturethen cooled in ice
  5. extractionThe product was extracted into ethyl acetate (3×300 ml)
  6. washthe combined extracts were washed with 20% aqueous sodium thiosulphate solution (3×300 ml)
  7. dry with materialthey were dried (MgSO4)
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6568e8890ac64fd8b755880c2f50b48d
Source dataset
uspto-grants-2006_12
Patent number
US07151102B2

Reaction notes

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