[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].CCN(CC)CC.[CH3:18][O:19][CH2:20]Cl>C(Cl)Cl.CCOC(C)=O>[CH3:18][O:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10]To a solution of 4-hydroxy-3-methylbenzaldehyde (900 mg, 6.61 mmol) in CH2Cl2 (19 mL) was added Et3N (5.90 mL, 42.3 mmol) and chloromethyl methyl ether (2.00 mL, 26.3 mmol). The reaction was stirred at 25° C. for 16 h. The reaction mixture was diluted with EtOAc and was successively washed with aqueous 1 N HCl solution, aqueous saturated NaHCO3 solution, water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 4:1) to give the title compound (630 mg, 53% yield) as a clear oil.
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