1-Naphthol → 1-Methoxynaphthalene

HRID 49693

Reaktionsgleichung

Reaktionsgleichung von HRID 49693
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]1CCN2C(=NCCC2)CC1>CCOC(C)=O.O>[CH3:12][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-naphthol (1.0 g, 6.94 mmol) in DMC (10 mL), DBU (1.06 g, 6.94 mmol) was added and the resulting mixture was heated to reflux (90° C.) for 16 hours. The reaction was cooled to ambient temperature and diluted with EtOAc (50 mL) and H2O (40 mL). The organic layer was separated and washed in sequence with 2M HCl (2×40 mL), 2M NaOH (2×40 mL) and H2O. The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give 1-methoxynaphthalene as an oil. The yield of 1-methoxynaphthalene as determined by HPLC was 99% conversion.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe organic layer was separated
  4. washwashed in sequence with 2M HCl (2×40 mL), 2M NaOH (2×40 mL) and H2O
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a5c9706326754e45afa5a3da0a92aedc
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706929B2

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