4-Hydroxybenzaldehyde → 4-Isopropoxybenzaldehyde

HRID 351817

Reaktionsgleichung

Reaktionsgleichung von HRID 351817
[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+].I[CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[CH:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

Produkt 1

HCID 2500774-IsopropoxybenzaldehydeAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2 g (16.38 mmol) of 4-hydroxybenzaldehyde in 100 mL of DMF, 2.72 g (19.69 mmol) of K2CO3, 2.74 g (16.52 mmol) of KI and 3.94 mL (39.38 mmol) of 2-iodopropane was added under argon. The mixture was stirred at 80° C. overnight, concentrated and the residue obtained was partitioned between CHCl3 and H2O. The phases were separated, the aqueous phase was extracted with CHCl3 and the combined organic phases were dried over MgSO4 and concentrated. The crude product obtained was purified by chromatography on silica gel using EtOAc/hexane mixtures of increasing polarity as eluent, to give 2.08 g of the title compound of the example as an oil (77% yield).

Aufarbeitung

  1. concentrationconcentrated
  2. customthe residue obtained
  3. customwas partitioned between CHCl3 and H2O
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CHCl3
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product obtained
  9. customwas purified by chromatography on silica gel
  10. temperatureof increasing polarity as eluent

Quellen und Nachweise

ORD-Eintrag
ord-894b4acbbcc04531b679f4df06420873
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743816B2

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