Methanol → 1-(4-chlorophenyl)-1,3-Propanediol

HRID 341792

Reaktionsgleichung

Reaktionsgleichung von HRID 341792
C([O:3][C:4](=O)[CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.[H-].C([Al+]C(C)C)(C)C.CO.O>C(Cl)Cl>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]([OH:14])[CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoateHCID 21896610Diisopropylaluminium hydride

Produkt 1

HCID 103300821-(4-chlorophenyl)-1,3-PropanediolAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5.0 g of ethyl-4-chlorobenzoylacetate in 100 ml of methylene chloride cooled to -30° C., 77.3 ml of diisopropylaluminium hydride (1.0 mol/l toluene solution) was added, and the resulting mixture was stirred for 30 minutes and then brought back to room temperature over 3 hours, and 4.14 g of methanol and 24.3 g of water were added carefully, and the mixture was stirred for another 1.5 hours. The precipitate was filtered off, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/1), to obtain 2.45 g of the title compound as a pale yellow oily substance.

Aufarbeitung

  1. waitbrought back to room temperature over 3 hours
  2. stirringthe mixture was stirred for another 1.5 hours
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-bbbe2d4035484addbe187122e4fa8725
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856327

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