[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>C(=S)=S.C(OCC)(=O)C>[C:18]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]To a solution of 10.00 g (60.2 mM) of fluorene in 100 ml of dry carbon disulfide, 9.40 g (70.5 mM) of anhydrous aluminum chloride was added while being cooled on an ice-common salt bath. Under cooling on the bath, 10.3 ml (60.3 mM) of octanoylchloride was gradually added dropwise to the mixture at -2.5° to 1° C., followed by stirring for 2 hours and 50 minutes without cooling on the bath. After the reaction, the reaction mixture was poured into a mixture of 150 g of ice and 50 ml of hydrochloric acid. To the resultant mixture, 100 ml of ethyl acetate was added, followed by stirring at room temperature to precipitate a crystal. The crystal was recovered by filtration and recrystallized from acetone to obtain 3.70 g of 2-octanoylfluorene. The organic layer separated from the filtrate was washed with water, dried with anhydrous sodium sulfate, and condensed into about 100 ml of the resultant solution, followed by cooling on an ice bath to precipitate a crystal. The crystal was recovered by filtration and recrystallized from acetone to obtain 4.09 g of 2-octanoylfluorene. The total amount of 2-octanoylfluorene obtained was 7.79 g (Yield: 44.3%).
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