Water → (2E)-3-[4-(Propan-2-yl)phenyl]prop-2-en-1-ol

HRID 1017854

Reaktionsgleichung

Reaktionsgleichung von HRID 1017854
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](OCC)=[O:13])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[CH2:12][OH:13])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 643831732580-69-1HCID 21226445Aluminium lithium hydride

Produkt 1

HCID 21961314(2E)-3-[4-(Propan-2-yl)phenyl]prop-2-en-1-olAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of ethyl (E)-3-(4-isopropylphenyl)-2-propenoate (20.0 g, 91.6 mmol) in tetrahydrofuran (200 ml) was added in four portions at −40° C. for 30 minutes lithium aluminum hydride (2.61 g, 68.7 mmol) and the resulting mixture was stirred at the same temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (hexane-ethyl acetate 8:1) to obtain 10.5 g (65% yield) of the oily title compound.

Aufarbeitung

  1. extractionthe product was extracted twice with ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d146ac1c3fd74b0fbf4f29ae41cef248
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479536B1

Verknüpfte Notizen

Wird geladen…