Iodoethane → 2-Ethoxy-1,3-dimethoxybenzene
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[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[OH:11].[OH-].[Na+].[CH2:14](I)[CH3:15]>CS(C)=O.O>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:11][CH2:14][CH3:15][CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[OH:11].[OH-].[Na+].[CH2:14](I)[CH3:15]>CS(C)=O.O>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:11][CH2:14][CH3:15]To a stirred solution of 2,6-dimethoxyphenol (10 g) in dimethylsulfoxide (100 ml) under nitrogen was added a solution of sodium hydroxide (3.2 g) in water (20 ml). The mixture was warmed to 50° C., ethyl iodide (12.4 g) added, and stirring continued at 50° C. for 4 hours. The product was poured into 1 liter of water and the mixture extracted with diethyl ether. The extract was washed sequentially with 20% potassium hydroxide, water, and brine, and then dried over magnesium sulfate. Removal of the solvent under reduced pressure gave 1,3-dimethoxy-2-ethoxybenzene as a colorless oil (6.71 g).
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