[OH2:1].C(#N)C.[C:5]1([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)C=CC=CC=1.I([O-])(=O)(=O)=[O:27].[Na+]>ClCCl.O.[Ru](Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[CH:14]1([CH2:13][CH2:12][CH2:11][C:5]([OH:27])=[O:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1
To a flask containing 90 mL of water, 60 mL of acetonitrile and 60 mL of carbon tetrachloride is added 4.8 g (16.8 mmol) of 1-(3-phenylpropyl)cyclododecane, 50.0 g (0.25 mol) of sodium periodate and then 70 mg (0.3 mmol) of ruthenium trichloride hydrate. The reaction mixture is allowed to stir at room temperature overnight. The mixture is then taken up in dichloromethane and 1N HCl and the layers separated. The aqueous phase is washed 3 times with dichloromethane and the combined organic layers are dried over MgSO4 and the solvents evaporated. The residue is taken up in ether, filtered through Celite and the filtrate evaporated. The crude product is flash chromatographed using acidic silica gel and 30% ethyl acetate/hexanes to give 3.25 g of a white solid: NMR (CDCl3) δ 1.2-1.5 (m, 10H), 1.65 (m, 2tt), 2.35 (t, 2H, J=8 Hz).
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