C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])(=O)=O)=CC=1.[C:23]1([CH:30]=[CH:29][C:27]([OH:28])=[CH:26][CH:25]=1)[OH:24]>C(O)CCC.[Na].[Hg]>[CH2:21]([O:24][C:23]1[CH:30]=[CH:29][C:27]([OH:28])=[CH:26][CH:25]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]2.60 g (8.02 mM) of 10-undecenyl p-toluenesulfonate and 1.79 g (16.2 mM) of hydroquinone were well mixed with 3 ml of butanol under stirring. Into the solution, a solution of 0.419 (9.74 mM) of sodium amalgam dissolved in 6 ml of butanol, followed by 7 hours of heat-refluxing at 110° C. After the reaction, butanol was distilled off, followed by addition of water and extraction with ether. To the ether extract liquid was added anhydrous sodium sulfate for drying, followed by distilling-off of ether and purification by column chromatography (developer solvent: methylene chloride) to obtain 1.00 g (3.82 mM) of p-(10-undecenyl)oxyphenol. Yield: 47.6%.
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