[H-].[Na+].[O:3]1[CH2:7]CC[CH2:4]1.[Br:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[OH:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13].COCCl>C(OCC)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH2:4][O:3][CH3:7])[C:12]([O:14][CH2:15][CH3:16])=[O:13]5.5 g of sodium hydride was added to a tetrahydrofuran (300 ml) solution of 20.5 g of ethyl 3-bromo-4-hydroxybenzoate produced according to the method described in Monatsh. Chem.; 22; 1901; 437, with cooling with ice, and the reaction liquid was stirred for 30 minutes, and then, at the same temperature, 10 ml of chloromethyl methyl ether was added to the reaction liquid, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, and washed with water, and the aqueous layer was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting solid was suspended in hexane and then taken out through filtration to obtain the entitled compound as a white solid.
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