[H-].[Na+].[Cl:3][C:4]1[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:17][O:18][CH2:19]Cl.O>CN(C)C=O>[Cl:3][C:4]1[C:14]([O:15][CH2:17][O:18][CH3:19])=[CH:13][CH:12]=[C:11]([Cl:16])[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]To a suspension of sodium hydride (60% in oil, 474 mg) in N,N-dimethylformamide (2 ml) was added a solution of ethyl 2,6-dichloro-3-hydroxybenzoate (2.42 g) in N,N-dimethylformamide (10 ml) under nitrogen at ambient temperature and the mixture was stirred for 1 hour at the same temperature. Chloromethyl methyl ether (1.15 ml) was added thereto and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:8, V/V) to give ethyl 2,6-dichloro-3-(methoxymethoxy)benzoate (2.58 g) as an oil.
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