[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1C=CC(C([O-])=O)=C[CH:9]=1.ClCCOCCO.[OH:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=1These compounds were synthesized by a similar method. The representative synthesis of 4-(2-(2-hydroxyethoxy)ethoxy)benzoate (3) is presented. A solution of 2-(2-chloro ethoxy)ethanol 5.338 grams (0.04 mole) in 50 ml of acetonitrile was added dropwise to a solution of methyl 4-hydroxybenzoate 5.1 grams (0.036 mole) and 23.2 grams (0.168 mole) of powdered anhydrous potassium carbonate in 300 ml of acetonitrile at 80° C. After stirring the reaction mixture under reflux for 12 hours, 250 ml of the acetonitrile was then distilled and 250 ml dichloromethane was added. The reaction mixture was filtered through CELITE® and the solid was washed thoroughly with dichloromethane. Evaporation of the filtrate yielded product in the form of a yellow oil. Purification by flash chromatography on silica gel with 40% diethyl ether in dichloromethane yielded 7.1 g (87%). 1H-NMR (CDCl3, TMS): d=2.62 (s, 1H, --OH), 3.81-4.25 (m, 8H, --(OCH2CH2)2 --), 3.85 (s, 3H, --COOCH3), 6.9 and 7.9 (2d, 4 aromatic protons).
불러오는 중…
