[H-].[Na+].[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:10]([OH:17])=[CH:9][C:8]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH3:4].Cl[CH2:23][C:24]([CH3:26])=[CH2:25].[Cl-].[NH4+]>CN(C)C=O>[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:11][C:10]([O:17][CH2:25][C:24]([CH3:26])=[CH2:23])=[CH:9][C:8]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH3:4]60% Oily sodium hydride (0.18 g) was suspended in N,N-dimethylformamide (10 ml). A solution of 4-acetoxy-3,5-di-tert-butylphenol (1 g) in N,N-dimethylformamide (5 ml) was added dropwise to the suspension under ice cooling and the mixture was stirred for 30 min. Subsequently, the reaction mixture was allowed to warm to room temperature and 3-chloro-2-methyl-1-propene (0.45 ml) was added dropwise. After stirring at room temperature for 2 h, a saturated aqueous solution of ammonium chloride (15 ml) was added to the reaction mixture. The mixture was subjected to extraction with diethyl ether and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-1-(2-methyl-2-propenyloxy)benzene [1.08 g (yield, 90%)] as a colorless liquid.
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