Dimethyl Sulfate → 2-Methoxy-6-(1-methylethyl)naphthalene
Reaktionsgleichung
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:8]=2)[CH:3]=1.[OH-].[Na+].[CH3:17]OS(OC)(=O)=O>O>[CH3:17][O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:8]=2)[CH:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a suspension of 31.71 g 2-hydroxy-6-(1-methylethyl)naphthalene in 500 ml water and under a nitrogen atmosphere was added 61.5 g of 14.4% (by weight) sodium hydroxide (NaOH). The mixture was heated to 60° C. and 30.02 g of dimethylsulfate was added in one portion to the dark cloudy solution. In 20 minutes the pH of the reaction had dropped from 13 to 2. Another 20 g 14.4% NaOH was added. After 45 minutes 10 g additional dimethylsulfate was added. After 1 hour 20 g of 14.4% NaOH was added and the reaction was heated at 80° C. overnight. The brown suspension was then extracted with toluene and the extract was dried over magnesium sulfate (MgSO4), filtered, and concentrated in vacuum to give a crude solid which was recrystallized from isopropanol to give 2-methoxy-6-isopropylnaphthalene, melting point 63.5° to 64.5° C.
Aufarbeitung
- additionIn 20 minutes the pH of the reaction had dropped from 13 to 2
- temperaturethe reaction was heated at 80° C. overnight
- extractionThe brown suspension was then extracted with toluene
- dry with materialthe extract was dried over magnesium sulfate (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuum
- customto give a crude solid which
- customwas recrystallized from isopropanol
Quellen und Nachweise
- ORD-Eintrag
- ord-dea392d0f63244949da540bfeef8e20a
- Quelldatensatz
- uspto-grants-1994_02
- Patentnummer
- US05286902
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