Water → 3-[4-(2-Acetoxypropyl)benzoyl]propionic acid

HRID 465452

Reaktionsgleichung

Reaktionsgleichung von HRID 465452
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12]([O:15][CH:16]([CH3:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:14])[CH3:13].O>ClCCCl>[C:12]([O:15][CH:16]([CH3:24])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:4]([CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[O:5])=[CH:20][CH:19]=1)(=[O:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7922Succinic anhydrideHCID 16457Benzeneethanol, alpha-methyl-, 1-acetateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 198745493-[4-(2-Acetoxypropyl)benzoyl]propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

Succinic anhydride (3 g) was added, under a nitrogen atmosphere, to a stirred slurry of aluminium chloride (8.25 g) in 1,2-dichloroethane (50 ml). The resulting mixture was stirred at room temperature for 15 minutes. A solution of 2-acetoxypropyl benzene (5 g) in 1,2-dichloroethane (20 ml) was added, dropwise, to the stirred mixture which was stirred for a further 3 days at room temperature. The reaction mixture was poured into water. The organic solvent was evaporated and the aqueous residue was extracted into ethyl acetate. The organic extract was washed with 2N HCl and extracted into dilute sodium bicarbonate solution. The aqueous extract was acidified with 2N HCl and extracted into ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to an oil which was chromatographed on silica gel. Elution with petroleum ether(60-80) - diethyl ether(50:50) gave 3-[4-(2-acetoxypropyl)- benzoyl]propionic acid as an oil.

Aufarbeitung

  1. stirringdropwise, to the stirred mixture which was stirred for a further 3 days at room temperature
  2. customThe organic solvent was evaporated
  3. extractionthe aqueous residue was extracted into ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with 2N HCl
  6. extractionextracted into dilute sodium bicarbonate solution
  7. extractionThe aqueous extract
  8. extractionextracted into ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated to an oil which
  12. customwas chromatographed on silica gel
  13. washElution with petroleum ether(60-80) - diethyl ether(50:50)

Quellen und Nachweise

ORD-Eintrag
ord-89758db16555407ca248c9a833421d50
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153210

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