[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C([O-])([O-])=O.[K+].[K+].Cl[CH2:19][O:20][CH3:21]>CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:19][O:20][CH3:21])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]To 1-(2,4-dihydroxyphenyl)ethanone (1.52 g, 10 mmol) in 12 mL acetone was added K2CO3 (1.38 g, 10 mmol) followed by slow addition of chloro(methoxy)methane (885 mg, 11 mmol) with stirring under Ar atmosphere at rt. The reaction mixture was stirred at rt for 4 h and filtered. Solid was washed with EtOAc (80 mL) and the combined filtrate was washed with NaH2PO4 (sat. 50 mL) and water (80 mL) and dried over MgSO4 and concentrated. The crude product was purified with silica chromatography (hexane/EtOAc) to afford 1-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone as a off-white solid (1.2 g, 61%). MS (ESI) m/z 197 (M+H+).
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