[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[Br:22].C(OCC)(=O)C.[H][H]>[C].[Ru].C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][C:13]=1[Br:22]A 500 ml capacity stainless steel autoclave was charged with 35 g (0.085 mol) of 2,2'-dibromo-1,1'-binaphthyl, 5.25 g of 5%-ruthenium-carbon (manufactured by NECHEMCAT), 130 ml of ethyl acetate and 130 ml of 95% ethanol. After carrying out 20 hours of hydrogenation at a temperature of 100° C. under a hydrogen pressure of 50 kg/cm2, absorption of 4 mols of hydrogen per mol substrate was confirmed. The reaction mixture was cooled to 30° C. to remove the catalyst by filtration, the resulting filtrate was allowed to stand overnight at room temperature and then 30.6 g of the thus precipitated crystals were collected by filtration (yield, 85.7%).
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