[C:1]1([CH3:16])[CH:6]=CC(S(OCC(C)CC)(=O)=O)=[CH:3][CH:2]=1.[C:17]1([CH:24]=[CH:23][C:21]([OH:22])=[CH:20][CH:19]=1)[OH:18].[OH-].[Na+]>O.C(O)CCC>[CH3:6][CH:1]([CH2:2][CH3:3])[CH2:16][O:18][C:17]1[CH:24]=[CH:23][C:21]([OH:22])=[CH:20][CH:19]=1Into a n-butanol suspension containing 37 mmol (9.0 g) of 2-methylbutyl p-toluenesulfonate prepared by tosylating S-(-)-2-methylbutanol and 74 mmol (8.2 g) of hydroquinone, added dropwise was a solution of 50 mmol (2.1 g) of sodium hydroxide dissolved in a solvent mixture comprising 3 ml of water and 10 ml of n-butanol, and the obtained mixture was then stirred for 8 hours at 120° C. After addition of water, the reaction solution was extracted with ether, and the extracted solution was dried and concentrated. The resulting concentrate was purified by column chromatography to obtain 4.8 g of the objective ether compound (Yield: 72%).
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