[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([C:20](OC)=[O:21])[CH2:17][CH:16]2[CH2:18][CH:9]1[CH:10]1[CH:15]2[CH:14]2[CH2:19][CH:11]1[CH:12]=[CH:13]2.[OH-].[K+].Cl>O1CCCC1>[CH3:7][C:8]1([CH2:20][OH:21])[CH2:17][CH:16]2[CH2:18][CH:9]1[CH:10]1[CH:15]2[CH:14]2[CH2:19][CH:11]1[CH:12]=[CH:13]2
37.6 g of lithium aluminum hydride and 800 ml of tetrahydrofuran were added to a flask and maintained at 0° C. in a nitrogen atmosphere. Then, 200 g of 8-methyl-8-methoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene dissolved in 200 ml of tetrahydrofuran was added from a dripping funnel over one hour, followed by a reaction for 2.5 hours at 70° C. The reaction solution was allowed to cool to room temperature and a 10% aqueous solution of potassium hydroxide was added gradually, followed by further addition of 10% aqueous solution of hydrochloric acid. The reaction solution was then extracted with toluene and the reaction product was salted out from saturated brine. The salt-out product was washed several times with water and dried over anhydrous magnesium sulfate. Toluene was evaporated to obtain 145 g of a white solid of 8-methyl-8-hydroxymethyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene shown by the following formula (19).
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