Dimethyl Sulfate → 2-Methoxy-4-[(3-methyl-2-buten-1-yl)oxy]benzaldehyde

Reaktionsgleichung

[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:20][O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

Versuchsvorschrift

10.6 g (206 mmol) of 2-hydroxy4-(3-methylbut-2-enyloxy)benzaldehyde and 5.4 ml of dimethyl sulfate were dissolved in 102 ml of distilled acetone, the solution was added 25.5 g of potassium carbonate, and the resulting mixture was refluxed for 5 hours. The mixture was filtered and the filtrate concentrated in vacuo to give 8.3 g of an yellow oil from which 5.4 g of 2-methoxy4-(3-methylbut-2enyloxy)benzaldehyde was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 400 g) using petroleum ether-ethyl acetate (9:1, 1000 ml), (4:1, 500 ml) as eluents.