Hydroquinone → 1,4-dihexyloxybenzene

Reaktionsgleichung

[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Na+].[I-]>C(O)C>[CH2:9]([O:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:7][CH2:8][CH2:1][CH2:3][CH2:4][CH3:5])=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

Versuchsvorschrift

Under argon atmosphere, 6.90 g (300 mmol) of Na is reacted with 200 ml of absolute ethanol. Then, 16.5 g (150 mmol) of hydroquinone 5 is added, followed by 42.2 ml (300 mmol) of hexylbromide and 200 mg of anhydrous NaI. The mixture is refluxed overnight. Ethanol is evaporated under reduced pressure and water (150 ml) is added. The product is extracted with dichloromethane and dried over MgSO4. After filtration, the solvents are removed and the crude compound is recrystallized from ethanol.