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

HRID 377541Notes

Reaction equation

HRID 377541 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

A solution of 5.00 g of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate was slowly added dropwise to a solution of 9.60 g (0.072 mol) of lithium iodide and 70 ml of dry pyridine at reflux temperature. After the reaction mixture had been stirred for 2 hours under reflux it was cooled, and the solvent was removed in vacuo. The residue was subsequently taken up in water and brought to pH 1-2 using dilute hydrochloric acid. After the aqueous phase had been extracted with ethyl acetate, the combined organic phases were washed to neutrality with water, dried and concentrated. This gave 4.00 g of 2-chloro-3-formyl-4-methylsulfonylbenzoic acid (85% yield).

Workup

  1. temperatureat reflux temperature
  2. temperatureunder reflux it
  3. temperaturewas cooled
  4. customthe solvent was removed in vacuo
  5. extractionAfter the aqueous phase had been extracted with ethyl acetate
  6. washthe combined organic phases were washed
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4c2c7034c7e24ac2bf89a24831363015
Source dataset
uspto-grants-2000_02
Patent number
US06028035

Reaction notes

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