[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18][C@@H:19]([CH2:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O>O.C(O)C>[CH3:18][C@@H:19]([CH2:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:17][C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:16][CH:15]=1A solution of NaOH (40 g) dissolved in water (18 ml) was added to a solution of p-benzyloxyphenol (12 g, 0.060 mol) dissolved in ethanol (60 ml), followed by dropwise adding to the mixture, (S)-6-methyloctyl-p-toluenesulfonate (16.7 g, 0.055 mol) obtained above, refluxing the resulting mixture for 12 hours, distilling off ethanol after completion of the reaction, extracting the residue with toluene, washing the resulting ortanic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, drying the layer, distilling off the organic solvent to obtain an oily product, and subjecting this product to column chromatography with activated alumina (17 g) to obtain (S)-p-benzyloxyphenyl 6-methyloctyl ether (15 g), dissolving this product (15 g, 0.046 mol) in ethanol (43 ml), subjecting the solution to hydrogenolysis in the presence of paradium-carbon (1.5 g) to obtain (S)-p-6-methyloctyloxyphenol (XII) (8.2 g).
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