p-Toluenesulfonic acid → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 478993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478993
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C@@H:5]([OH:9])[C:6]([OH:8])=[O:7].[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:13][O:7][C:6](=[O:8])[C@@H:5]([C:4]1[CH:10]=[CH:11][CH:12]=[C:2]([Cl:1])[CH:3]=1)[OH:9]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Produkt 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Into methanol (20 ml) were added (R)-3-chloromandelic acid (5.0 g) and p-toluenesulfonic acid (0.1 g), and the resulting mixture was heated under reflux for 2 hours. The reaction mixture was cooled, then neutralized and concentrated. Ethyl acetate and water were added to the resulting residue and the organic layer was collected by layer separation. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off to obtain a colorless oily compound mentioned above (5.27 g, 98.3%).

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. additionEthyl acetate and water were added to the resulting residue
  6. customthe organic layer was collected by layer separation
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. filtrationThe desiccant was filtered off
  10. distillationthe solvent was distilled off
  11. customto obtain a colorless oily compound

Quellen und Nachweise

ORD-Eintrag
ord-001f1fb4da98422885262d5473d04cdb
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642395B1

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