[CH:1]12[CH2:11][CH:7]([C:8](=[O:10])[CH2:9]1)[CH:6]1[CH:2]2[CH2:3][CH2:4][CH2:5]1.[CH3:12][Mg]Cl.O>O1CCCC1>[CH3:12][C:8]1([OH:10])[CH2:9][CH:1]2[CH2:11][CH:7]1[CH:6]1[CH:2]2[CH2:3][CH2:4][CH2:5]1Tricyclo [5.2.1.02,6] decan-8-one (15.0 g) in tetrahydrofuran (THF, 50 ml) is slowly added into CH3MgCl (9.7 g) in THF and the reaction mixture is stirred completely. Tetrahydrofuran (THF, 100 ml) with 5% of water is added into the reaction mixture. Then 100 ml of water is added to the reaction mixture. The reaction mixture is extracted by ether. The organic extract is concentrated in vacuo to yield 8-methyl-tricyclo [5.2.1.02,6] decan-8-ol (formula (X)) as white solid.
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