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.O[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.[H-].[Na+].[OH2:39]>C(O)CCC>[CH2:21]([O:36][C:33]1[CH:34]=[CH:35][C:30]([C:27]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[C:31]([OH:39])[CH:32]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]The above-prepared 2.60 g (8.02 mM) of 10-undecenyl p-toluenesulfonate, 3.0 g (16.0 mM) of dihydroxybiphenyl and 3 ml of butanol were mixed and sufficiently stirred. To the mixture, a solution of 0.41 g (9.74 mM) of sodium hydride in 6 ml of butanol was added, followed by heat-refluxing for 7 hours at 110° C. After the reaction, the reaction mixture was subjected to distilling-off of butanol and addition of water, followed by extraction with ether to obtain an extract. The extract was dried with anhydrous sodium sulfate, followed by distilling-off of ether and purification by column chromatography (eluent: methylene chloride) to obtain 1.55 g (3.82 mM) of p-(10-undecenyl)oxyhydroxybiphenyl (Yield: 47.6%).
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