Iodine → 5-Iodo-2,4-dimethylbenzoic acid

HRID 1487815Notes

Reaction equation

HRID 1487815 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]([O-])(=O)(=O)=O.[Na+].II.S(=O)(=O)(O)O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)(=O)C.O>[I:12][C:8]1[C:9]([CH3:11])=[CH:10][C:2]([CH3:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 118972,4-Dimethylbenzoic acidHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodate

Product 1

HCID 230918755-Iodo-2,4-dimethylbenzoic acidYield 162.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2,4-dimethylbenzoic acid (20.0 g, 133 mmol), sodium periodate (14.27 g, 66.72 mmol), iodine (37.25 g, 146.8 mmol), and sulfuric acid (1.96 g, 20.0 mmol) in acetic acid (150 mL) was stirred at 110° C. for 6 h. The mixture was allowed to cool to ambient temperature then carefully diluted into water (1.2 L). To this mixture was carefully added saturated aqueous Na2S2O3 (800 mL). The resulting solids were collected by filtration, then dissolved in ethyl acetate (1.2 L) and washed with saturated aqueous Na2S2O3 (300 mL) followed by brine (400 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue was re-crystallized from ethanol:H2O (2:1) to yield the title compound as a white solid (30 g, 82%).

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. dissolutiondissolved in ethyl acetate (1.2 L)
  3. washwashed with saturated aqueous Na2S2O3 (300 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was re-crystallized from ethanol:H2O (2:1)

Sources & evidence

ORD record
ord-fc6300cd60a941668c8b1d9d41198bbb
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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