Water → 2,7-Dimethoxynaphthalene

HRID 394648

Reaktionsgleichung

Reaktionsgleichung von HRID 394648
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[CH:3]=1.S([O:18][CH3:19])(OC)(=O)=O.[C:20](=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:20][O:12][C:6]1[CH:7]=[CH:8][C:9]2[C:4](=[CH:3][C:2]([O:18][CH3:19])=[CH:11][CH:10]=2)[CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 113972,7-NaphthalenediolHCID 11430Potassium Carbonate

Produkt 1

HCID 770212,7-Dimethoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Methylation of 2,7-dihydroxynaphthalene (10 g: 62.43 mmol) is carried out in acetone (100 ml) in the presence of dimethyl sulphate (12.06 ml:127 mmol:2.03 eq.) and dry potassium carbon-ate (42.3 g:306 mmol:4.9 eq.). The temperature of the reaction medium is 56° C. for 6 hours and then 40° C for 12 hours. Hydrolysis (7.4 ml of water) requires 2 hours of stirring at ambient temperature. After filtering off the salts over Celite and concentrating the remaining filtrate, extraction with dichloromethane yields an organic phase, which, after evaporation, has the appearance of a beige solid. The latter is rendered colourless using active carbon and then recrystallised from a PE/CH2Cl2 mixture.

Aufarbeitung

  1. wait40° C for 12 hours
  2. waitrequires 2 hours
  3. filtrationAfter filtering off the salts over Celite
  4. concentrationconcentrating
  5. extractionthe remaining filtrate, extraction with dichloromethane
  6. customyields an organic phase, which
  7. customafter evaporation
  8. customrecrystallised from a PE/CH2Cl2 mixture

Quellen und Nachweise

ORD-Eintrag
ord-dd140a32cc9244b59abc998ddefd0ee4
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602903B2

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