9H-Fluorene-9,9-dimethanol

Dimethylsulfoxide (DMSO) (300 ml), toluene (300 ml) and paraformaldehyde (PF) (40 gram) were charged into a round bottom flask, mixed and cooled to a temperature of 13-15 °C. Subsequently, sodium methoxide 30 percent solution (26 gram) was added to this mixture.Gradually fluorene in powder form (100 gram, 0.6 mole) was added to above reaction mixture over a period of 15 minutes, while the temperature was maintained at 14-16 °C. It was observed that most of the paraformaldehyde dissolves instantly upon addition of the fluorene. The resulting mixture was stirred for 30 minutes while the temperature was maintained at 14-16 °C. The resulting mixture was a clear pale yellowsolution.Subsequently, concentrated HCI (8-10 ml) was added to the obtained solution until al neutral pH (pH 6-7) was reached in order to stop the reaction. To the reaction mass gradually water (1000 ml) is added and reaction mass is cooled to 10 °C for 3 hours.The solid product was obtained by filtration. The solid product was filtered and washed with chilled toluene (two times 25 ml). The solid product was kept under vacuum till the toluene was completely removed from the product. The wet weight of the solid product was 120 gram. The product is then dried at 60-70 °C and weighed again. The dry weight was 90-95 gram. The yield was 70percent. The purity of the product as determined by HPLC was >98 percent. The melting point was 139-144 00.Dimethylsulfoxide (DMSO) (400 ml) and paraformaldehyde (PF) (40 gram) werecharged into a round bottom flask, mixed and cooled to a temperature of 13-15 00.Subsequently, sodium methoxide 30 percent solution (26 gram) was added to this mixture.Gradually fluorene in powder form (100 gram) was added to above reaction mixture over a period of 15 minutes, while the temperature was maintained at 14-16 00 It was observed that most of the paraformaldehyde dissolves instantly upon addition of the fluorene. The resulting mixture was stirred for 30 minutes while the temperaturewas maintained at 14-16 00 The resulting mixture was a clear pale yellow solution.Subsequently, concentrated HCI (8-10 ml) was added to the obtained solution until al neutral pH (pH 6-7) was reached in order to stop the reaction. The following work up was carried out for the reaction mixture: a large 3-5 liter round bottom flask wascharged with water (1200 ml). The reaction mixture was slowed added to the water under stirring. The resulting mixture was stirred for 30 minutes at room temperature. The solid crude reaction product was obtained by filtration.To the crude product toluene (350 ml) was added. The mixture was heated to80-90 00 The heating was stopped and the mixture was allowed to return to roomtemperature. Then the mixture was further cooled to 10 00 and maintained at that temperature for 2 hours. The solid product was filtered and washed with chilled toluene (two times 25 ml). The solid product was kept under vacuum till the toluene was completely removed from the product. The wet weight of the solid product was150 gram. The product is then dried at 60-70 00 and weighed again. The dry weight was 85-93 gram. The yield was 69percent. The purity of the product as determined by HPLC was >98 percent. The melting point was 139-144 00Dimethylsulfoxide (DMSO) (300 ml) and paraformaldehyde (PF) (25 gram) were charged into a round bottom flask, mixed and cooled to a temperature of 13-15 °C. Subsequently, sodium methoxide 30 percent solution (3.5 gram) was added to this mixture. A solution of fluorene (50 gram) in DMSO (300 ml) was added to above reaction mixture over a period of 1 -2 minutes, while the temperature was maintained at 14- 16 °C. The resulting mixture was stirred for 15 minutes while the temperature was maintained at 14-16 °C. The resulting mixture was a clear pale yellow solution. Subsequently, concentrated HCI (5-10 ml) was added to the obtained solution until al neutral pH (pH 6-7) was reached in order to stop the reaction. The following work up was carried out for the reaction mixture: a large 3-5 liter round bottom flask was charged with water (1200 ml). The reaction mixture was slowed added to the water under stirring. The resulting mixture was stirred for 15-30 minutes at room temperature. The crude reaction product was obtained by extraction with ethyl acetate. The organic phase is dried and distilled under vacuum. The residue was crystallized in 200 ml toluene to get the product as off white crystals. The dry weight was 25 gram. The yield was 30percent. The purity of the product as determined by HPLC was >98 percent.Dimethylsulfoxide (DMSO) (300 ml), toluene (300 ml) and paraformaldehyde (PF) (40 gram) were charged into a round bottom flask, mixed and cooled to a temperature of 13-15 C. Subsequently, sodium methoxide 30 % solution (26 gram) was added to this mixture.Gradually fluorene in powder form (100 gram, 0.6 mole) was added to above reaction mixture over a period of 15 minutes, while the temperature was maintained at 14-16 C. It was observed that most of the paraformaldehyde dissolves instantly upon addition of the fluorene. The resulting mixture was stirred for 30 minutes while the temperature was maintained at 14-16 C. The resulting mixture was a clear pale yellowsolution.Subsequently, concentrated HCI (8-10 ml) was added to the obtained solution until al neutral pH (pH 6-7) was reached in order to stop the reaction. To the reaction mass gradually water (1000 ml) is added and reaction mass is cooled to 10 C for 3 hours.The solid product was obtained by filtration. The solid product was filtered and washed with chilled toluene (two times 25 ml). The solid product was kept under vacuum till the toluene was completely removed from the product. The wet weight of the solid product was 120 gram. The product is then dried at 60-70 C and weighed again. The dry weight was 90-95 gram. The yield was 70%. The purity of the product as determined by HPLC was >98 %. The melting point was 139-144 00.Dimethylsulfoxide (DMSO) (400 ml) and paraformaldehyde (PF) (40 gram) werecharged into a round bottom flask, mixed and cooled to a temperature of 13-15 00.Subsequently, sodium methoxide 30 % solution (26 gram) was added to this mixture.Gradually fluorene in powder form (100 gram) was added to above reaction mixture over a period of 15 minutes, while the temperature was maintained at 14-16 00 It was observed that most of the paraformaldehyde dissolves instantly upon addition of the fluorene. The resulting mixture was stirred for 30 minutes while the temperaturewas maintained at 14-16 00 The resulting mixture was a clear pale yellow solution.Subsequently, concentrated HCI (8-10 ml) was added to the obtained solution until al neutral pH (pH 6-7) was reached in order to stop the reaction. The following work up was carried out for the reaction mixture: a large 3-5 liter round bottom flask wascharged with water (1200 ml). The reaction mixture was slowed added to the water under stirring. The resulting mixture was stirred for 30 minutes at room temperature. The solid crude reaction product was obtained by filtration.To the crude product toluene (350 ml) was added. The mixture was heated to80-90 00 The heating was stopped and the mixture was allowed to return to roomtemperature. Then the mixture was further cooled to 10 00 and maintained at that temperature for 2 hours. The solid product was filtered and washed with chilled toluene (two times 25 ml). The solid product was kept under vacuum till the toluene was completely removed from the product. The wet weight of the solid product was150 gram. The product is then dried at 60-70 00 and weighed again. The dry weight was 85-93 gram. The yield was 69%. The purity of the product as determined by HPLC was >98 %. The melting point was 139-144 00Dimethylsulfoxide (DMSO) (300 ml) and paraformaldehyde (PF) (25 gram) were charged into a round bottom flask, mixed and cooled to a temperature of 13-15 C. Subsequently, sodium methoxide 30 % solution (3.5 gram) was added to this mixture. A solution of fluorene (50 gram) in DMSO (300 ml) was added to above reaction mixture over a period of 1 -2 minutes, while the temperature was maintained at 14- 16 C. The resulting mixture was stirred for 15 minutes while the temperature was maintained at 14-16 C. The resulting mixture was a clear pale yellow solution. Subsequently, concentrated HCI (5-10 ml) was added to the obtained solution until al neutral pH (pH 6-7) was reached in order to stop the reaction. The following work up was carried out for the reaction mixture: a large 3-5 liter round bottom flask was charged with water (1200 ml). The reaction mixture was slowed added to the water under stirring. The resulting mixture was stirred for 15-30 minutes at room temperature. The crude reaction product was obtained by extraction with ethyl acetate. The organic phase is dried and distilled under vacuum. The residue was crystallized in 200 ml toluene to get the product as off white crystals. The dry weight was 25 gram. The yield was 30%. The purity of the product as determined by HPLC was >98 %.In a reaction bottle, Nitrogen protection and anhydrous conditions, Was added 9, 9-dimethylolfluorene (2.9 g)Triethylamine (11 mL) and tetrahydrofuran (80 mL).Under cooling was added dropwise over 1 hour triallyl chlorosilane (5.6 g) and tetrahydrofuran (20mL) of the mixture, after the addition reaction at room temperature for 4 hours. Heated to reflux for 6 hours.After completion of the reaction, the solution was cooled, filtered, washed three times with diethyl ether, Combine organic phase, The dried solvent was dried over anhydrous sodium sulfate for 24 hours.

Molecular Weight:226.27
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:226.099379685
Monoisotopic Mass:226.099379685
Topological Polar Surface Area:40.5
Heavy Atom Count:17
Complexity:248
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes