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

HRID 541189Notes

Reaction equation

HRID 541189 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 g, 133.18 mmol, 1.00 equiv), sodium periodate (14.27 g, 66.72 mmol, 0.50 equiv), iodine (37.25 g, 146.76 mmol, 1.10 equiv), and sulfuric acid (1.96 g, 19.98 mmol, 0.15 equiv) in acetic acid (150 mL) was stirred at 110° C. in an oil bath. After 6 h, the reaction mixture was allowed to reach ambient temperature and was then diluted with 1.2 L of water. To this was carefully added 800 mL of aq Na2S2O3 (aq., sat.). The resulting solids were collected by filtration, dissolved in 1.2 L of ethyl acetate, and washed with 1×300 mL of Na2S2O3 (aq., sat.) followed by 1×400 mL of brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude residue was re-crystallized from ethanol:H2O (2:1) to yield 30 g (82%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-71925f748cbd4e50a6e93e09ecaac4a8
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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