C[O:2][C:3]([C:5]1[C:19]2=[C:20]3[C:12]([C:13]4[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:11][CH:10]=[CH:9][C:8]3=[CH:7][CH:6]=1)=O.[Li+].[BH4-].C1COCC1.Cl>O>[OH:2][CH2:3][C:5]1[C:19]2=[C:20]3[C:12]([C:13]4[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:11][CH:10]=[CH:9][C:8]3=[CH:7][CH:6]=1To a RB flask equipped with magnetic stirrer, condenser, and N2 inlet line with bubbler was added methyl-1-fluoranthenecarboxylate (3A, 71.54 g, 0.275 mol), LiBH4 (Aldrich, 100 g, 0.459 mol) and dry THF (1 L). The mixture was refluxed overnight, cooled and poured into H2O (2 L). The mixture was cautiously acidified with 1N HCl, filtered and the resulting solid washed with H2O (2×300 mL). After recrystallization (CH2Cl2 /hexane) and drying, 54.75 g (86%) of 1-hydroxymethylfluoranthene was obtained, mp 147°-185°, (C,H).
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