Potassium Hydroxide → 3-Iodo-2-methyl-4-methylsulfonylbenzoic Acid

HRID 848977Notes

Reaction equation

HRID 848977 reaction equation
[OH-].[K+].[I:3][C:4]1[C:5]([CH3:19])=[C:6]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:7]([O:9]CC)=[O:8]>O.C(O)C>[I:3][C:4]1[C:5]([CH3:19])=[C:6]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21183139Ethyl 3-iodo-2-methyl-4-methylsulfonylbenzoate

Product 1

HCID 211831523-Iodo-2-methyl-4-methylsulfonylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 18.2 g (276 mmol) of 85 percent potassium hydroxide in 100 mL of water was added to a mixture of 67.8 g (184 mmol) of ethyl 3-iodo-2-methyl-4-methylsulfonylbenzoate in 300 mL of ethanol with stirring. After about 1 hour, all of the solids had dissolved and after 2 hours the mixture was concentrated by evaporation under reduced pressure. The residue obtained was diluted with water and the solution obtained was extracted with ether and then diluted with ethyl acetate. Aqueous hydrochloric acid (3N) was then added until the mixture was acidic. The organic phase was separated and the aqueous phase was twice extracted with ethyl acetate. The organic phase and extracts were combined and washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The 62.1 g (99 percent of theory) of colorless solid residue was the title compound. The purified compound melts at 193° C.

Workup

  1. dissolutionall of the solids had dissolved and after 2 hours the mixture
  2. concentrationwas concentrated by evaporation under reduced pressure
  3. customThe residue obtained
  4. customthe solution obtained
  5. extractionwas extracted with ether
  6. additiondiluted with ethyl acetate
  7. additionAqueous hydrochloric acid (3N) was then added until the mixture
  8. customThe organic phase was separated
  9. extractionthe aqueous phase was twice extracted with ethyl acetate
  10. washwashed with saturated aqueous sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-adcdf1b459f4403c8dd7ce7c5fd1b584
Source dataset
uspto-grants-2000_01
Patent number
US06010981

Reaction notes

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