[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:11]=1)[CH:2]=[CH2:3]Allyl bromide (2.30 g) was added to a stirred suspension of ethyl 3-(4-hydroxyphenyl)propionate (3.49 g) and anhydrous potassium carbonate (2.76 g) in butan-2-one (30 ml). The reaction mixture was heated at reflux for 18 hours. The reaction mixture was allowed to cool to ambient temperature and the mixture was filtered. The filtrate was evaporated to give an oil which was purified by column chromatography on silica gel (Merck.Art. No. 9385) using a 4:1 (v/v) mixture of n-hexane and ethyl acetate as eluent to give ethyl 3-(4-allyloxyphenyl)propionate (4.09 g) as a colourless oil; NMR (CDCl3): 1.22 (3H, t), 2.48 (2H, t), 2.88 (2H, t), 4.13 (2H, q), 4.51 (2H, m), 5.25-5.42 (2H, m), 5.95-6.15 (1H, m), 6.83 (2H, d) and 7.03 (2H, d); m/z 235 (M+H).
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