Allyl bromide → Methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate

Reaktionsgleichung

[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][C:6]([CH3:19])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:5][C:6]([CH3:19])([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:3][CH:2]=[CH2:1])=[CH:16][CH:17]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

Versuchsvorschrift

Allyl bromide (0.66 ml) was added to a stirred suspension of methyl 2,2-dimethyl-3-(4-hydroxyphenyl)propionate (1.41 g) and potassium carbonate (1.08 g) in butan-2-one (12 ml). The reaction mixture was heated at reflux for 19 hours, cooled, and filtered. The filtrate was evaporated to give methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate (1.59 g) as an oil; NMR(CDCl3): 1.17(6H,s), 2.78(2H,s), 3.65(3H,s), 4.50(2H,m), 5.33(2H,m), 6.02(1H,m), 6.70(2H,m) and 7.00(2H,m); m/z 248(M+).