OC1C=CC(C2C=CC(O)=CC=2)=CC=1.[OH-].[K+].CC(CC)CBr.[CH3:23][C@@H:24]([CH2:45][CH3:46])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([O:39]C[C@@H](C)CC)=[CH:35][CH:34]=2)=[CH:29][CH:28]=1.Cl>C(O)C>[OH:39][C:36]1[CH:35]=[CH:34][C:33]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:25][C@@H:24]([CH3:23])[CH2:45][CH3:46])=[CH:28][CH:29]=2)=[CH:38][CH:37]=1A mixture of 4,4'-dihydroxybiphenyl (500 g), ethyl alcohol (7.5 l) and potassium hydroxide (302 g) was heated with stirring under reflux, and (+)-2-methylbutylbromide (prepared from (-)-2-methylbutanol and phosphorus bromide) (530 g) was dropwise added to carry out reaction for 4 hours, followed by distilling off ethanol, adding water (2 l), filtering, collecting insoluble matter, adding toluene to this insoluble matter to dissolve and remove toluene-soluble matter (this soluble matter, when recrystallized from ethyl alcohol, gave scaly crystals having a m.p. of 80.5° C.; thus the compound was confirmed to be 4,4'-di((S)-2-methylbutyloxy)biphenyl), heating the insoluble matter together with 3N-hydrochloric acid with stirring, cooling solid matter and recrystallizing from toluene and then from ethyl alcohol to obtain 4-hydroxy-4'-((S)-2-methylbutyloxy)biphenyl (XXI) having a m.p. of 137.5° C. (125 g).
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