Water → 2,3-Diisopropoxy-4-methoxybenzaldehyde

HRID 9308

Reaktionsgleichung

Reaktionsgleichung von HRID 9308
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]([O-])([O-])=O.[K+].[K+].Br[CH:20]([CH3:22])[CH3:21].O.CCO[C:27]([CH3:29])=O>CN(C=O)C>[CH:20]([O:1][C:2]1[C:9]([O:10][CH:27]([CH3:29])[CH3:13])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:22])[CH3:21]

Komponenten

7

Edukt 5

HCID 962WaterHCID 63582-BromopropaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 115573522,3-Dihydroxy-4-methoxybenzaldehyde

Produkt 1

HCID 219865542,3-Diisopropoxy-4-methoxybenzaldehydeAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 21 (26.70 g, 158.7 mmol) in DMF (150 mL) under nitrogen, was added K2CO3 (65.84 g, 476.3 mmol) followed by 2-bromopropane (44.72 mL, 476.3 mmol) and heated to reflux (90° C.) for 12 hours. Water (200 mL) and EtOAc (200 mL) were added to the reaction mixture, the phases were separated, and the aqueous phase was extracted with EtOAc (3×200 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexane) provided 32.85 g (1.30.2 mmol, 82%) of the diusopropyl-protected aldehyde 22 as a yellow oil.

Aufarbeitung

  1. temperatureheated
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (3×200 mL)
  4. dry with materialThe combined organic solutions were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washby flash column chromatography (silica gel, elution with hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fcacfd8cbe564e93b9260f019b289944
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091240B2

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