Lithium iodide → 2-Chloro-3-formyl-4-methylsulfonylbenzoic acid

HRID 1368813Notes

Reaction equation

HRID 1368813 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

Product 1

HCID 185174222-Chloro-3-formyl-4-methylsulfonylbenzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At reflux temperature, a solution of 5.00 g (0.018 mol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate was added dropwise to a solution of 9.60 g (0.072 mol) of lithium iodide and 70 ml of dry pyridine. After stirring under reflux for 2 hours, the reaction mixture was cooled and the solvent was removed under reduced pressure. The residue was then taken up in water and adjusted to pH 1-2 with dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water until neutral, dried and concentrated. 4.00 g of 2-chloro-3-formyl-4-methylsulfonylbenzoic acid (85% yield) were obtained.

Workup

  1. temperatureAt reflux temperature
  2. temperatureunder reflux for 2 hours
  3. temperaturethe reaction mixture was cooled
  4. customthe solvent was removed under reduced pressure
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phases were washed with water until neutral,
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9d6d483bc0674239a443633d4411df70
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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