[H-].[Na+].CCCCCC.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl>C(OCC)(=O)C.O>[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:18][C:15]1[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=1To 200 mg (0.5 mmol) of sodium hydride (60% dispersion in oil) was added 10 mL of hexane. After settling, the hexane was decanted. To the residue was added 10 mL of freshly distilled tetrahydrofuran and the slurry mixture was cooled at 0° C. To this was added slowly 200 mg (1.43 mmole) of 4-nitrophenol (20) as a solid portionwise. The reaction mixture was stirred at 0° C. for 5 minutes and 197 μL (1.71 mmol) of 2-methoxyethoxy methyl chloride was added. The mixture was stirred at room temperature for 18 hours. To the reaction mixture 25 mL of water was slowly added and the reaction mixture was diluted with 50 mL of ethyl acetate. The organic part was separated and the aqueous layer was extracted with 2×50 mL of ethyl acetate. The organic layers were combined and washed with 7×100 mL of saturated sodium carbonate solution, followed by 100 mL of water. The ethyl acetate layer was dried over MgSO4 and concentrated to yield 225 mg (0.99 mmol, 69%) of 1-[(2-methoxyethoxy)methoxy]-4-nitrobenzene (21) as a pale yellow oil. NMR, IR and MS data confirmed compound identity.
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