Hydrochloric Acid → 2-Benzyloxy-4-cyanobenzaldehyde

HRID 1985834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1985834
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[OH:11])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CN(C)C=O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH:1]=[O:2])[C:7]#[N:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 128136484-Formyl-3-hydroxybenzonitrile

Produkt 1

HCID 189739062-Benzyloxy-4-cyanobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Formyl-3-hydroxybenzonitrile (4.0 g) and potassium carbonate (3.76 g) were suspended in N,N-dimethylformamide (20 mL). To the reaction mixture was added benzylbromide (3.6 mL), and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give the title compound (3.0 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-430c30e25103493795672ec87b624abd
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547680B2

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