[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:13])[CH2:11][CH3:12].C(N(C(C)C)CC)(C)C.Cl[CH2:24][O:25][CH3:26]>ClCCl>[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:24][O:25][CH3:26])[CH:5]=[CH:4][C:3]=1[C:10](=[O:13])[CH2:11][CH3:12]To a mixture composed of 1-(2,4-dihydroxy-3-methylphenyl)propan-1-one (5.00 g, 27.8 mmol) and dichloromethane (80 mL), diisopropylethylamine (5.26 mL, 30.5 mmol) was added under cooling with ice, and then a solution of chloro(methoxy)methane (2.30 mL, 30.5 mmol) in dichloromethane (20 mL) was added dropwise to the mixture over 20 minutes. After the completion of dropwise addition, the mixture was brought back to room temperature and stirred overnight. Dichloromethane was added to the reaction solution. The organic layer was washed with water and then dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=90/10→70/30) to obtain 5.73 g of the title compound (yield: 92%).
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