[BH4-].[Na+].[CH3:3][CH:4]1[C:12](=[O:13])[C:11]2[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]=[CH:7][C:6]=2[CH2:5]1.O>CO>[OH:13][CH:12]1[C:11]2[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]=[CH:7][C:6]=2[CH2:5][CH:4]1[CH3:3]Sodium borohydride (7.5 g) was added portion-wise at 0-20° C. to a solution of 18.1 g of 2,3-dihydro-2-methyl-benz[e]indene-1-one in 200 ml of methanol. The reaction was completed after 15 min of stirring, and the reaction mixture was poured into 400 ml of water. The organic layer was separated, and the water layer was extracted with diethyl ether. The combined organic layers were washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. The crude product was recrystallized from cyclohexane to obtain 14.3 g (78%) of 2,3-dihydro-1-hydroxy-2-methyl-1H-benz[e]indene.
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