4-Hydroxybenzaldehyde → 4-(Cyclopropylmethoxy)benzaldehyde

HRID 1485056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485056
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]1[CH2:20][CH2:19]1>CC(C)=O>[CH:18]1([CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Produkt 1

HCID 5432414-(Cyclopropylmethoxy)benzaldehydeAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of 4-hydroxybenzaldehyde (2.00 g), potassium carbonate (4.53 g) and acetone (50.0 mL), (bromomethyl)cyclopropane (3.32 g) was added and the mixture was refluxed for 9 hours. After cooling the reaction mixture to room temperature, the resulting precipitate was removed by filtration through Celite (registered trademark). The filtrate was concentrated under reduced pressure and, thereafter, the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-50:50) to give the titled compound as a colorless oil (2.63 g).

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed for 9 hours
  3. customthe resulting precipitate was removed by filtration through Celite (registered trademark)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-50:50)

Quellen und Nachweise

ORD-Eintrag
ord-7126be6f684c46649b6767ebd4077f8c
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422240B2

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