[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH:2]=C.OCCOCC[O:27][C:28]1C=CC(C([O-])=O)=[CH:30][CH:29]=1.[H-].[Na+].[H][H].C(Br)C=C>O1CCCC1.O>[CH2:28]([O:27][CH2:2][CH2:1][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH:29]=[CH2:30]
These compounds were synthesized by similar methods. The representative synthesis of methyl 4-(2-(2-allyloxy-ethoxy)ethoxy)benzoate (7) is presented. The obtained methyl 4-(2-(2-hydroxyethoxy) ethoxy) benzoate (3) 8.4 grams (0.035 mole) was added to a suspension of 3.15 grams (0.105 mole) sodium hydride in 100 ml dried tetrahydrofuran at 4° C. After the hydrogen was completely released, allyl bromide 3.94 ml (0.0456 mole) was added dropwise to the reaction mixture and then stirred at room temperature overnight. The excess sodium hydride was treated with distilled water and extracted with ethyl acetate. The organic phase was washed with 10% aqueous hydrochloric acid solution, dried over anhydrous MgSO4, and the solvent evaporated on a rotary evaporator. The yellow oil product was purified by flash chromatography on silica gel with 4% diethyl ether in dischloromethane. Yield 8.39 grams (86%). 1H-NMR (CDCl3, TMS): d=3.81-4.25 (m, 10H, --CH2 --(OCH2CH2)2 --), 3.85 (s, 3H, --COOCH3), 5.23 and 5.9 (m, 3H, CH=CH--), 6.95 and 8.05 (2d, 4 aromatic protons).
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