[Mg].[CH3:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.BrCCBr.[Br-].[CH2:22](Br)[CH:23]=[CH2:24]>O1CCCC1.C(OCC)C.C1C=CC=CC=1>[CH3:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:24][CH:23]=[CH2:22])=[CH:12][CH:11]=1
Magnesium turnings (0.83g, 0.032 mol) and 10 mL of anhydrous tetrahydrofuran (THF) were placed in a dry 3-necked round bottom flask. The mixture was stirred under reflux in an argon atmosphere for about 20 minutes. The previously prepared 4-[2-(2-methoxyethoxy)ethoxy]bromobenzene (7-Og, 0.025 mol) in 30 mL of anhydrous THF was slowly dripped into the stirring magnesium mixture. A small amount (about 0.1 mL) of 1,2-dibromoethane was initially added to start the Grignard reaction. After the bromide was added, the mixture was refluxed overnight under an argon atmosphere. The mixture was then cooled to -78° C. and 15 mL (0.17 mol) of allyl bromide in 30 mL of spectral grade benzene was added. The resulting mixture was stirred and allowed to slowly warm to room temperature and then refluxed overnight. The mixture was cooled and exacted with ethyl ether. The ethyl ether layer was washed with aqueous 3N hydrochloric acid, aqueous saturated brine and then with water until the organic layer was neutral. The ethyl ether solution was dried over anhydrous magnesium sulfate and the solvent was removed. The product was distilled to give 2.78 g (47%) of the desired 3-(4-[2-(2-methoxyethoxy) ethoxy]phenyl]-1-propene, bp 105°-113° C./0.2mm; NMR(δ): 3.30(2H,d), 3.36(3H,s), 3.46-3.92(6H,m), 4.12(2H,m), 5.00(2H,m), 5.95(1H,m), 6.80(2H,d), 7.04(2H,d).
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