Reaction SMILES: C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([CH2:21][CH3:22])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br>C(O)C.[Ni].C(O)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([CH2:21][CH3:22])[CH2:17][CH2:16]3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1
Reactant: CC[C@H]1CC[C@H]([C@H]2CC[C@H](c3ccc(OC)cc3)CC2)CC1
Agent: [Ni]
Agent: Br
Solvent: CC(=O)O
Solvent: CCO
Product: CC[C@H]1CC[C@H]([C@H]2CC[C@H](c3ccc(O)cc3)CC2)CC1

Procedure:
Potassium hydrogen sulfate (6 g) was added to it, followed by dehydrating at 160° C. for 2 hours in nitrogen current, cooling, adding toluene (200 ml), filtering off potassium hydrogen sulfide, washing the toluene layer with water till the washing liquid became neutral, distilling off toluene under reduced pressure and recrystallizing the remaining oily substance from ethanol to obtain 4-methoxy-[4-(trans-4-ethylcyclohexyl)cyclohexen-1-yl]benzene. This material (70 g) was dissolved in ethanol (120 ml) together with Raney Ni catalyst (1.0 g) and subjected to catalytic reduction under ordinary pressure at 50° C. to absorb hydrogen (500 ml), followed by filtering off the catalyst and recrystallizing as it was. Since the resulting material was a mixture of cis-form and trans-form substances, it was further repeatedly recrystallized from ethanol to isolate the trans-form substance. The resulting 4-methoxy-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]benzene (80 g) was dissolved in acetic acid (450 ml), and hydrobromic acid (47%) (450 ml) was added, followed by reflux for 30 hours. After the reaction the reaction liquid was cooled and crystals were deposited and filtered off, followed by recrystallizing the crystals from ethanol to obtain 4-hydroxy-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]benzene. This material (20 g) was placed in an autoclave and ethanol (400 ml) was added and further Ru/C (3 g) was added to carry out catalytic reduction under 50 Kg/cm2 at 180° C., followed by filtering off the catalyst and distilling off the solvent under reduced pressure to obtain 4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]cyclohexanol. To this material was added acetone (8 l), and a solution (50 ml) obtained by adding water to anhydrous chromic acid (14.5 g) and conc. sulfuric acid (23.6 g) was dropwise added over 2 hours while the temperature was kept at 0° C.~3° C. After completion of the reaction, an excess amount of the oxidant was decomposed by adding isopropyl alcohol, followed by further adding sodium hydrogen carbonate for neutralization, filtering off the resulting precipitate, washing it with acetone, combining the filtrate and the washing liquid together, distilling off acetone under reduced pressure, extracting three times with toluene (500 ml), drying combined toluene layers with sodium sulfate, distilling off toluene under reduced pressure, and recrystallizing from fresh toluene (50 ml) to obtain 4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]cyclohexanone (XII), which was then dried in vacuo on heating. This material (11.6 g) was dissolved in tetrahydrofuran (100 ml) and the solution was rapidly dropwise added to a solution of 4-methylbenzenemagnesium bromide obtained by reacting Mg piece (1.2 g) with p-bromotoluene (8.38 g). After reflux for 3 hours, the reaction liquid was cooled and 3N hydrochloric acid was added, followed by extracting with toluene (300 ml), repeating water-washing till the washing liquid became neutral, distilling off the solvent under reduced pressure, adding potassium hydrogen sulfate (4 g) to the remaining oily substance, dehydrating at 160° C. for 2 hours in nitrogen atmosphere, cooling, filtering off potassium hydrogen sulfate, adding toluene (300 ml), washing with water, distilling off the solvent under reduced pressure, and recrystallizing from fresh toluene (70 ml) to obtain an objective product, 4-methyl-{4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]cyclohexen-1-yl}benzene (yield: 4.6 g) having a C-Sm point of 59.4° C., a Sm-N point of 234° C. and a N-I point of 284° C.