Water → 4-(Hexyloxy)naphthalene-1-carbaldehyde

HRID 2092957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092957
O=P(Cl)(Cl)Cl.[CH2:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:23](O[Na])(C)=[O:24].O>CN(C=O)C>[CH2:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=[O:24])=[CH:15][CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 30172091-(Hexyloxy)naphthaleneHCID 178418247HCID 178418247, Verbindung

Produkt 1

HCID 30169154-(Hexyloxy)naphthalene-1-carbaldehydeAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

POCl3 (3.22 g, 21 mmol) was dropwise added to a solution of compound 2 (4 g, 17.5 mmol) in anh. DMF (5 ml) at room temperature and under N2. The resulting dark red solution was heated to 100° C. for 3 hours. Concentrated AcONa solution (5 ml) was then added and heating was continued for 2 hours more. After being cooled to room temperature, water (100 ml) was added. The mixture was extracted with Et2O (2×150 ml), the ethereal combined fractions were washed with 10% HCl solution (100 ml), water (100 ml), dried over MgSO4, filtered and evaporated to dryness. Recrystallisation of the brown solid from EtOH afford 2.1 g (47%) of compound 3 as brownish crystals.

Aufarbeitung

  1. temperatureheating
  2. temperatureAfter being cooled to room temperature
  3. extractionThe mixture was extracted with Et2O (2×150 ml)
  4. washwere washed with 10% HCl solution (100 ml), water (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customRecrystallisation of the brown solid from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-b052e601d3e74469b1292572f120e6f1
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440843B2

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