Pyridine → 4-(4-Isopropoxyphenoxy)benzaldehyde

HRID 404879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404879
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Br[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>[O-2].[Cu+2].ClCCl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 820014-Isopropoxyphenol

Produkt 1

HCID 877217474-(4-Isopropoxyphenoxy)benzaldehydeAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 164827Copper oxide (CuO)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of Example 17A (1.50 g, 9.86 mmol), 4-bromobenzaldehyde (2.20 g, 11.9 mmol.), (K2CO3 (2.85 g, 20.6 mmol) and pyridine (50 mL) at 80° C. was added Cu(II) oxide (1.95 g, 24.5 mmol). After the addition, the mixture was refluxed vigorously for 20 hours. After cooling, dichloromethane was added and the mixture was filtered through Celite. The filtrate was concentrated to dryness. The residue was dissolved in ether, which was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×), dried over MgSO4, and concentrated to dryness. The residue was purified on silica gel eluting with a hexane and ethyl acetate gradient to give the desired product as a white solid (1.42 g, 56%).

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed vigorously for 20 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in ether
  7. washwhich was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified on silica gel eluting with a hexane and ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag
ord-d9dd6c9633f04085bc54f055c08be427
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748627B2

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