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

HRID 1368813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1368813
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9d6d483bc0674239a443633d4411df70
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06576596B1

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