1-Methoxynaphthalene → 4-Methoxy-1-naphthaldehyde

HRID 619871

Reaktionsgleichung

Reaktionsgleichung von HRID 619871
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.[C:18]([O-])(=[O:20])C.[Na+]>CN(C)C=O>[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=[O:20])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 166681-MethoxynaphthaleneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Produkt 1

HCID 852174-Methoxy-1-naphthaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phosphorus oxychloride (315 g, 1.6 mole) was added dropwise over 4 hours to a stirred solution of 1-methoxynaphthalene (250 g) (2) in dried dimethylformamide (150 g). the reaction mixture was heated on a water bath for a further 4 hours, cooled, and poured onto ice (1 k) and 2M aqueous sodium acetate (1.5 l). The organic layer was extracted with dichloromethane (1 l) and washed with dilute hydrochloric acid and then with water. The organic layer was dried (MgSO4), filtered, and the solvent removed. 4-Methoxy-1-naphthaldehyde (3) was obtained as a pale yellow oil.

Aufarbeitung

  1. temperaturethe reaction mixture was heated on a water bath for a further 4 hours
  2. temperaturecooled
  3. extractionThe organic layer was extracted with dichloromethane (1 l)
  4. washwashed with dilute hydrochloric acid
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-576ddbd5b879497aa317e9498f2aef28
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04818096

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