C1[CH2:5][O:4][CH2:3]C1.[Br:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[OH:18].[H-].[Na+].COCCl>O>[Br:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]([CH3:15])([CH3:17])[CH3:16])[C:8]=1[O:18][CH2:3][O:4][CH3:5]
Under nitrogen atmosphere, a THF 50 ml solution of 2-bromo-4-methyl-6-tert-butylphenol(23.41 g, 100 mmol) was added dropwise at 0° C. with stirring to a 100 ml THF suspension of sodium hydride (60%, 5.20 g, 130 mmol). After 2 hours, a THF 20 ml solution of methoxymethyl chloride (95%, 12.71 g, 150 mmol) was added dropwise to the mixture obtained above, the resulting mixture was brought up to room temperature and stirred for 10 hours. The reaction liquid thus obtained was cooled to 0° C., 100 ml of water was added thereto, and the aqueous layer was extracted with toluene (extracted twice with 200 ml of toluene). The organic solution layers were combined, washed with 100 ml of saturated aqueous sodium chloride solution, then dried with anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel column chromatography to obtain a colorless oil. The 1H-NMR spectrum data of the oil are shown below. The NMR data were determined by using EX-270 (mfd. by JEOL).
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