Citric Acid → 4-[(3-Chlorophenyl)thio]benzoic acid

HRID 401661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401661
[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59625879HCID 59625879, Verbindung

Produkt 1

HCID 157278294-[(3-Chlorophenyl)thio]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

A mixture of compound 30c (320 mg, 1.15 mmol), LiOH (110 mg, 4.59 mmol) in THF/MeOH/H2O (3/3/3 mL) was stirred for 4 h. A 15% aqueous citric acid solution (10 mL) was added. The mixture was then extracted with EtOAc (3×). The combined organic extracts were washed with brine, filtered, dried over Na2SO4, and concentrated under reduced pressure. The resultant residue (compound 30d, 290 mg) was dried under reduced pressure for 18 h and was used without further purification.

Aufarbeitung

  1. extractionThe mixture was then extracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with brine
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe resultant residue (compound 30d, 290 mg) was dried under reduced pressure for 18 h
  7. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-6a5689e55b4c47398be4561dbcf02689
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741887B2

Notizen zur Reaktion

Wird geladen…