[ CAS No. 3236-71-3 ] {[proInfo.proName]}

Name: 3236-71-3|4,4'-(9H-Fluorene-9,9-diyl)diphenol|98%
Brand: Ambeed
SKU: A158443
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Quality Control of [ 3236-71-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3236-71-3 ]

SDS Specification

Alternatived Products of [ 3236-71-3 ]

Product Details of [ 3236-71-3 ]

CAS No. :	3236-71-3	MDL No. :	MFCD00191392
Formula :	C₂₅H₁₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YWFPGFJLYRKYJZ-UHFFFAOYSA-N
M.W :	350.41	Pubchem ID :	76716
Synonyms :

Calculated chemistry of [ 3236-71-3 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.04
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	107.79
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.79
Log Po/w (XLOGP3) :	5.96
Log Po/w (WLOGP) :	5.46
Log Po/w (MLOGP) :	4.63
Log Po/w (SILICOS-IT) :	5.65
Consensus Log Po/w :	4.9

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.29
Solubility :	0.000178 mg/ml ; 0.000000509 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.59
Solubility :	0.000091 mg/ml ; 0.00000026 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.02
Solubility :	0.000000335 mg/ml ; 0.000000001 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.11

Safety of [ 3236-71-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	3077
Hazard Statements:	H315-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 3236-71-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3236-71-3 ]
Downstream synthetic route of [ 3236-71-3 ]

[ 3236-71-3 ] Synthesis Path-Upstream 1~10

1
[ 486-25-9 ]
[ 108-95-2 ]
[ 3236-71-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride In Zinc chloride; water; isopropyl alcohol	EXAMPLE 4 9,9-bis-(4-hydroxyphenyl)-fluorene 20 moles of phenol containing 9percent by weight of water were stirred in an autoclave and then one mole of zinc chloride and 10 moles of fluorenone were dissolved therein. Then, 5 moles of gaseous hydrogen chloride were added to the stirred mixture and the mixture was reacted at 70° C. for 4 hours. The reaction mixture was then dissolved in 5 liters of isopropanol at 60° C. and the solution was poured with vigorous stirring into a ten-fold volume of water to precipitate 3.4 kg of 9,9,-bis-(4-hydroxyphenyl)-fluorene (97percent yield in the form of a yellow product.
97%	With hydrogenchloride In Zinc chloride; water; isopropyl alcohol	EXAMPLE 5 9,9-bis-(4-hydroxyphenyl)-fluorene 40 moles of phenol containing 9percent by weight of water were stirred in an autoclave and 2 moles of zinc chloride and 10 moles of fluorenone were dissolved therein. Then, 10 moles of gaseous hydrogen chloride were added and the mixture was reacted for 4 days at room temperature. The reaction mixture was dissolved in 5 liters of isopropanol at 60° C. and the solution was poured with vigorous stirring into 10 fold volume of water to obtain 3,4 kg of 9,9-bis-(4-hydroxyphenyl)-fluorene (97percent yield) in the form of a light-yellow product of greater purity than Examples 3 and 4.
92.5%	With sulfuric acid; 3-mercaptopropionic acid In dichloromethane at 20 - 40℃; for 6 h;	To the equipped with a mechanical stirring, thermometer, condenser of 100 ml flask, adding 10 g 9 - fluorenone (0.055 µM), 31.5 g phenol (0.33 µM), 16 g dichloroethane, stirring is placed in the water bath, adding 2.5 g of concentrated sulfuric acid, to control the temperature 20 °C the left and the right, slowly adding 0 . 37 g 3 - mercapto propionic acid (0.0035 µM), after adding, in 20 °C reaction 2 hours, slowly raising the temperature to 30 °C continue to reaction 1 hours. System completely turn into a white color after shape fluid, sampling liquid phase analysis, 9 - fluorenone reaction is complete, the liquid phase content of 95percent (deduction of phenol). After adding 30 g of dichloroethane, to cool down to room temperature filtration, the filter cake is washed with a small amount of dichloroethane. Filter cake at the mass ratio of 1:1 of 5percent sodium hydroxide solution in a mashing, filtering, drying to obtain 18.3 g of pure white solid, yield 94.1percent, content is greater than 99.3percent. The combined organic filtrate is recycled.To the above-mentioned filtrate is sequentially added in 10 g 9 - fluorenone (0.055 µM), 11.5 g of phenol (0.12 µM), concentrated sulfuric acid 1.2 g, 0 . 12 g 3 - mercapto propionic acid (0.0013 µM) after 20 °C reaction 2 hours, heating to 40 °C reaction 1 hours. Until the system completely turn into a pure white slurry after the reaction, the sampling liquid phase analysis, 9 - fluorenone reaction is complete, the content 96.1percent (deduction of phenol). Cooling to room temperature filtering, washing, beating, filtering, drying to obtain about 18.0 g pure white solid, yield 92.5percent, the purity is greater than 99percent.

91%	at 110℃; for 3 h; Green chemistry	Accurately weigh 0.1 mol of anthrone and add it to a 250 mL three-necked flask, followed by0.4 mol of phenol and 0.010 mol of acidic ionic liquid N-(3-sulfopropyl)-2-indenyl The benzothiazole p-toluenesulfonatewas stirred and reacted at 110 ° C for 3 h.A sample was taken for liquid chromatography analysis, the conversion of anthrone was 100percent, andthe selectivity ofbisphenol oxime (9,9-bis(p-hydroxyphenyl)anthracene) was 94percent (as shown in Figure 1).The reaction solution was poured into a beaker while hot, and anappropriate amount of 20 ° C waterwas added to the beaker towash the ionic liquid, and the layer was allowed to stand. The ionic liquid catalyst was distilled off from the aqueous phase under reduced pressure; and90 ° C hot water was addedto the oily viscoussolid. After thorough mixing, the mixture was allowed to stand for separation, and the aqueous phase was separated from the oily viscous solid phase. The above operation was repeateduntil the hot phase was stirred at 90 ° C, and the solid phase was no longer viscous.The solid particles and the filtrate were obtained under reduced pressure, and the solid particleswere dried to obtain a bisphenol hydrazine product.The filtrate which was suction-filtered under reduced pressure was distilled under reduced pressure to obtain phenol, and the phenol recoverywas 80percent.The solid crude product was recrystallized from methylene chloride to give purified bisphenolphthalein in a yield of 91percent, and the purity of the bisphenol oxime wasmore than 99percent.
89%	at 90℃; for 6 h;	Preparation of bisphenolphthalein:Accurately weighedA certain amount of fluorenone, added to a 50 mL three-necked flask, then add the right amount of phenol,Ionic Liquid [(CH2)3SO3HBth][HSO4],At a temperature of 90°C,heating,Backflow 6h,After the reaction is over,Dip a suitable amount of reaction solution into CH3OH with a glass rod.Analyzed by liquid chromatography. Pour the reaction solution into the beakerAdd an appropriate amount of water at 20°C in the beaker to wash it.Stably layered,The upper layer is water phase,The lower layer is an oily viscous solid.Separating the aqueous phase from the oily viscous solid phase,The aqueous phase contains an ionic liquid catalyst and a small amount of phenol,Pending;Add 90°C hot water to the viscous solidStir with a glass rod,Stably layered,The upper layer is water phase,The lower layer is still an oily viscous solid,Separating the aqueous phase from the oily viscous solid phase,Repeat the above operation,After adding hot water at 90°C, stirThe solid phase is no longer viscous,Solids become granular,Stop the above operation.Decompression,Get solid particles and filtrate,Dry the solid particles,That is,Bisphenol quinone of crude product,The solid yield was 94percent.Recrystallization of bisphenolphthalein,The yield of bisphenolphthalein is 89percent.Product purity is greater than 99percent.
85%	With silica-gel-supported sulfuric acid; 3-mercaptopropionic acid In toluene at 30 - 45℃; for 3.5 h; Inert atmosphere	A solid acid H2SO4-SiO2 catalytic preparation of bisphenol fluorene process, the method comprises the following steps: 1) In a 1000 ml three-necked flask equipped with a thermometer, 50 g (0.275 mol) of 9-fluorenone was added under nitrogen atmosphere, phenol (157 g, 1.67 mol), toluene 50 ml, 1 g (0.01 mol) of 3-mercaptopropionic acid was added dropwise, after being completely dissolved by heating to 30 ° C, 16.6 g (8percent wt) of solid acid H2SO4-SiO2 was slowly added, after completion of the dropwise addition, the reaction was carried out at 45 ° C for 3.5 hours, after completion of the reaction, the solution A was analyzed for bisphenol fluorene content, 96.50percent (HPLC detection), the test results shown in Figure 2. 2) Solution A was hot filtered at 45 ° C to recover the solid acid, the filtrate was distilled to remove toluene, and then 100 ml of boiling water was added to the reaction flask to make two phases. Poured into 250 ml of ice water while vigorously stirred, the precipitated solid was suction filtered, the solid B and filtrate C were obtained. 3) Solid B was dried at 60 ° C for 2 hours, to obtain 91.5 g of bisphenol fluorene as a white solid powder, yield 98, purity 96.0percent; by toluene and methanol mixture solution (V toluene: V methanol = 10: 1) 275 ml recrystallization, filtered, 80 deg. C drying, a white crystalline bisphenol fluorene 80 grams, yield 85percent, purity 99.7percent;
85%	With methanesulfonic acid; 3-mercaptopropionic acid In toluene at 40℃; for 13 h; Inert atmosphere	Under a nitrogen atmosphere, 9-fluorene (138.7 mmol, 25.0 g), phenol (332.5 mmol, 31.29 g) was added to a 500 Ml reaction flask,3-Mercaptopropionic acid (13.8 mmol, 1.47 g) was added and toluene (140.5 g) was added. Methanesulfonic acid (276.7 mmol, 26.6 g) was added to the mixture, the temperature was gradually raised to 40 ° C, and the mixture was stirred at the same temperature for 13 hours. The reaction mixture was cooled to room temperature and then concentrated to remove toluene, 155.5 g of tetrahydrofuran was added and dissolved by stirring. After confirming dissolution, 198.7 g of methylene chloride was added, and the mixture was washed twice with 150.0 g of purified water, and concentrated to remove the solvent. 175.0 g of methanol was added, and the mixture was heated to reflux for 30 minutes. After cooling to 10 ° C, the mixture was stirred for 1 hour, filtered and dried to obtain the target compound, 9,9-bis (4-hydroxyphenyl) fluorene (1-1) (yield: 85percent).
85%	With methanesulfonic acid; 3-mercaptopropionic acid In toluene at 40℃; for 13 h; Inert atmosphere	Under a nitrogen atmosphere, 9-fluorene (138.7 mmol, 25.0 g), phenol (332.5 mmol, 31.29 g)3-mercaptopropionic acid(13.8 mmol, 1.47 g) was added and toluene (140.5 g) was added.To the mixture was added methanesulfonic acid(276.7 mmol, 26.6 g) was added thereto, the temperature was gradually raised to 40 ° C, and the mixture was stirred at the same temperature for 13 hours.The reaction mixture was cooled to room temperature and then concentrated to remove toluene,155.5 g of tetrahydrofuran was added and dissolved by stirring.After confirming dissolution, 198.7 g of methylene chloride was added, and the mixture was washed twice with 150.0 g of purified water and concentrated to remove the solvent.175.0 g of methanol was added, and the mixture was heated to reflux for 30 minutes. After cooling to 10 ° C, the mixture was stirred for 1 hour, filtered, and dried to obtain the target compound, 9,9-bis (4-hydroxyphenyl) fluorene (4-1)

Reference： [1] Patent: US4467122, 1984, A,
[2] Patent: US4467122, 1984, A,
[3] Patent: CN104693012, 2017, B, . Location in patent: Paragraph 0029-0038
[4] Patent: CN108570019, 2018, A, . Location in patent: Paragraph 0060; 0061; 0063; 0065; 0075
[5] Patent: CN107698429, 2018, A, . Location in patent: Paragraph 0032; 0034
[6] Patent: CN105693475, 2016, A, . Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035
[7] Patent: KR101692343, 2017, B1, . Location in patent: Paragraph 0082; 0083; 0084; 0085
[8] Patent: KR101716647, 2017, B1, . Location in patent: Paragraph 0104-0107
[9] Polymer, 2012, vol. 53, # 10, p. 2001 - 2007
[10] Organic Letters, 2006, vol. 8, # 13, p. 2787 - 2790

2
[ 486-25-9 ]
[ 108-95-2 ]
[ 620-92-8 ]
[ 3236-71-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride In Zinc chloride; water; isopropyl alcohol	EXAMPLE 3 9,9-bis-(4-hydroxyphenyl)-fluorene 30 moles of phenol containing 9percent by weight of water were stirred in an autoclave and then 2 moles of zinc chloride and 10 moles of fluorenone were dissolved therein. Then, 10 moles of gaseous hydrogen chloride were added to the stirred mixture and the mixture was reacted at 80° C. for one hour and then at 70° C. for 3 hours. The reaction mixture was then dissolved in 5 liters of isopropanol at 60° C. and the solution was then poured with vigorous stirring into a ten-fold volume of water whereby the resulting bisphenol precipitated as 3.4 kg (97percent yield) of the product in the form of a yellow product.

Reference： [1] Patent: US4467122, 1984, A,
[2] Patent: US4467122, 1984, A,

3
[ 117766-40-2 ]
[ 3236-71-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 7, p. 1212 - 1218

4
[ 486-25-9 ]
[ 107-96-0 ]
[ 108-95-2 ]
[ 3236-71-3 ]

Reference： [1] Patent: US5447960, 1995, A,

5
[ 486-25-9 ]
[ 3236-71-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 7, p. 1212 - 1218

6
[ 486-25-9 ]
[ 108-95-2 ]
[ 3236-71-3 ]

Reference： [1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 1837 - 1838
[2] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 1837 - 1838

7
[ 3236-71-3 ]
[ 3957-22-0 ]

Reference： [1] Patent: US2012/115084, 2012, A1,

8
[ 75-21-8 ]
[ 3236-71-3 ]
[ 117344-32-8 ]

Yield	Reaction Conditions	Operation in experiment
91.5%	With potassium hydroxide In water; isopropyl alcohol at 30 - 65℃; for 6.83333 h;	A 500 mL pressure reaction vessel was added 35 g of bisphenol fluorene, 200 ml of isopropanol, 1.5 g of potassium hydroxide dissolved in 1.5 ml of an aqueous solution, installed reactor, stirred into the cooling water, stirred open, open heating, temperature was raised to 30 , start of passing 10.5 g of ethylene oxide (pass once every 5 minutes), which leads to 50 minutes, then pass into the finished, temperature was raised to 65 , for 6 hours. After the reaction, the reaction solution was poured into 500 ml beaker, allowed to stand for cooling the precipitate is then filtered off with suction, the liquid ethanol recovered for reuse next, the solid was recrystallized from 154 ml of toluene after which the solid was dried 2, dissolved by heating to 85 , standing to cool to precipitate, filtration and drying, to obtain 40.0 g bis-fluorenyl ether as a white solid, yield 91.5percent, LC purity of 98.5percent obtained characterization, platinum cobalt color 15 Hazen around.

Reference： [1] Patent: CN106478381, 2017, A, . Location in patent: Paragraph 0025

9
[ 96-49-1 ]
[ 3236-71-3 ]
[ 117344-32-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium fluoride In N,N-dimethyl-formamide for 4 h; Inert atmosphere; Reflux	100 g (285.3 mmol) of bis (4-hydroxyphenyl) fluorene (1-1) obtained in the step 1 of Example 1, 500 ml of DMF, 52.7 g (599.0 mmol) of ethylene carbonate, 1 g of KF was added and the mixture was subjected to a reflux reaction for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and 1 L of purified water was added thereto, followed by stirring for 20 minutes. After 1 L of methylene chloride was added, the mixture was stirred for 30 minutes, and the organic layer was separated.(Yield: 75percent),
75%	With potassium fluoride In N,N-dimethyl-formamide for 4 h; Inert atmosphere; Reflux	Under a nitrogen atmosphere, 100.0 g (285.3 mmol) of bis (4-hydroxyphenyl) fluorene (4-1) obtained in the step 1 of Example 4,DMF (500 ml), ethylene carbonate52.7 g (599.0 mmol),KF 1gAnd the mixture was refluxed for 4 hours.After completion of the reaction, the reaction mixture was cooled to room temperature and 1 L of purified water was added thereto, followed by stirring for 20 minutes. After 1 L of methylene chloride was added, the mixture was stirred for 30 minutes, and the organic layer was separated. Washed with 1 L of purified water four times, and the organic layer was concentrated to obtain the target [yield 75

Reference： [1] Patent: KR101692343, 2017, B1, . Location in patent: Paragraph 0095; 0096; 0097; 0098
[2] Patent: KR101716647, 2017, B1, . Location in patent: Paragraph 0114-0117

10
[ 75-21-8 ]
[ 3236-71-3 ]
[ 117344-32-8 ]

Yield	Reaction Conditions	Operation in experiment
98.0 %Chromat.	at 100℃; for 12 h;	[0152] Reaction of adding EO to bisphenol fluorene (BPF) was carried out in the similar manner as in Example 1 except for the following. Specifically, into an autoclave, charged were 100 g of BPF, 200 g of ethyleneglycol monomethyl ether (δ=11.4), and 10.0 g of anion exchange resin A (Cl-type dried material), with addition of 31 g of EO. Next, the mixture was reacted in the autoclave at 100° C. for 12 hours. After the reaction, the anion exchange resin A was separated from the reaction solution. [0153] A result of GC analysis on the composition of the reaction solution reveals that the content of BPF-2EO was 97.1percent, and the content of BPF-3EO was 2.7percent, respectively. No BPF and BPF-1EO were detected. [0154] EXAMPLE 11; After letting the reaction solution obtained in Example 10 stand at 25° C., a white solid was precipitated. The solid was recovered and dried. A result of GC analysis on the composition of the reaction solution reveals that the content of BPF-2EO was 98.0percent, and the content of BPF-3EO was 2.0percent, respectively. The yield of BPF-2EO was 60percent.

Reference： [1] Patent: US2004/181099, 2004, A1, . Location in patent: Page 14

[ 3236-71-3 ] Synthesis Path-Downstream 1~88

1
[ 3236-71-3 ]
[ 110299-21-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1953 - 1956
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2175 - 2178

2
[ 3236-71-3 ]
[ 59507-02-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide; In acetone; at 50℃; for 4h;	0.01 Mole of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong>, 0.02 mole of NaOH and 100 mL of acetone were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 50 C. for 4 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 50 mL of hot acetone, and then dried under reduced pressure at 250 C. for 3 hrs, to yield 37 g of bis-sodium salt of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong>. The yield was 94%, and the purity was 99.8%.

Reference： [1]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 3
[2]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1953 - 1956
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2175 - 2178

3
[ 3236-71-3 ]
9,9-bis(4'-hydroxyphenyl)fluorene disulphate diammonium salt [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1045 - 1052

4
[ 31643-49-9 ]
[ 3236-71-3 ]
[ 72741-99-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	9,9-Bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride(FLDA) was synthesized according to the literature using a threestepsynthetic procedure starting from the nitro-displacement reactionof 4-nitrophthalonitrile with <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong>, in dryN,N-dimethylformamide (DMF), in the presence of potassium carbonate,at room temperature, followed by alkaline hydrolysis of thetetranitrile intermediate and dehydration with acetic anhydride of theresulting tetracarboxylic acid [25,26]. M.p.: 252-254 C. FTIR (KBr,cm-1): 1840, 1775, 1600, 1248. 1H NMR (400 MHz, DMSO-d6, delta): 7.11(4H, m), 7.28 (4H, m), 7.45 (4H, m), 7.52 (4H, m), 7.75 (2H, d), 7.97(2H, m), 8.02 (2H, d).

Reference： [1]Revue Roumaine de Chimie,2005,vol. 50,p. 579 - 587
[2]Polyhedron,2011,vol. 30,p. 522 - 528
[3]Reactive and functional polymers,2016,vol. 103,p. 17 - 25

5
[ 486-25-9 ]
[ 108-95-2 ]
[ 3236-71-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride; In Zinc chloride; water; isopropyl alcohol;	EXAMPLE 4 9,9-bis-(4-hydroxyphenyl)-fluorene 20 moles of phenol containing 9% by weight of water were stirred in an autoclave and then one mole of zinc chloride and 10 moles of fluorenone were dissolved therein. Then, 5 moles of gaseous hydrogen chloride were added to the stirred mixture and the mixture was reacted at 70 C. for 4 hours. The reaction mixture was then dissolved in 5 liters of isopropanol at 60 C. and the solution was poured with vigorous stirring into a ten-fold volume of water to precipitate 3.4 kg of 9,9,-bis-(4-hydroxyphenyl)-fluorene (97% yield in the form of a yellow product.
97%	With hydrogenchloride; In Zinc chloride; water; isopropyl alcohol;	EXAMPLE 5 9,9-bis-(4-hydroxyphenyl)-fluorene 40 moles of phenol containing 9% by weight of water were stirred in an autoclave and 2 moles of zinc chloride and 10 moles of fluorenone were dissolved therein. Then, 10 moles of gaseous hydrogen chloride were added and the mixture was reacted for 4 days at room temperature. The reaction mixture was dissolved in 5 liters of isopropanol at 60 C. and the solution was poured with vigorous stirring into 10 fold volume of water to obtain 3,4 kg of 9,9-bis-(4-hydroxyphenyl)-fluorene (97% yield) in the form of a light-yellow product of greater purity than Examples 3 and 4.
92.5%	With sulfuric acid; 3-mercaptopropionic acid; In dichloromethane; at 20 - 40℃; for 6h;	To the equipped with a mechanical stirring, thermometer, condenser of 100 ml flask, adding 10 g 9 - fluorenone (0.055 muM), 31.5 g phenol (0.33 muM), 16 g dichloroethane, stirring is placed in the water bath, adding 2.5 g of concentrated sulfuric acid, to control the temperature 20 C the left and the right, slowly adding 0 . 37 g 3 - mercapto propionic acid (0.0035 muM), after adding, in 20 C reaction 2 hours, slowly raising the temperature to 30 C continue to reaction 1 hours. System completely turn into a white color after shape fluid, sampling liquid phase analysis, 9 - fluorenone reaction is complete, the liquid phase content of 95% (deduction of phenol). After adding 30 g of dichloroethane, to cool down to room temperature filtration, the filter cake is washed with a small amount of dichloroethane. Filter cake at the mass ratio of 1:1 of 5% sodium hydroxide solution in a mashing, filtering, drying to obtain 18.3 g of pure white solid, yield 94.1%, content is greater than 99.3%. The combined organic filtrate is recycled.To the above-mentioned filtrate is sequentially added in 10 g 9 - fluorenone (0.055 muM), 11.5 g of phenol (0.12 muM), concentrated sulfuric acid 1.2 g, 0 . 12 g 3 - mercapto propionic acid (0.0013 muM) after 20 C reaction 2 hours, heating to 40 C reaction 1 hours. Until the system completely turn into a pure white slurry after the reaction, the sampling liquid phase analysis, 9 - fluorenone reaction is complete, the content 96.1% (deduction of phenol). Cooling to room temperature filtering, washing, beating, filtering, drying to obtain about 18.0 g pure white solid, yield 92.5%, the purity is greater than 99%.

92.8%	With 3-mercaptopropionic acid; In chlorobenzene; for 5h;Reflux;	3.6 g of 9-fluorenone, 7.4 g of phenol, 3.4 g of activated clay catalyst, 0.2 g of 3-mercaptopropionic acid, 35 g of chlorobenzene were sequentially added to a three-pack equipped with a stirrer, a thermometer and a water separator (with a condenser) In the flask, the mixture was stirred, heated to reflux and separated, and the reaction time was 5 hours. After the reaction, the mixture was filtered while hot, and the residue was recovered for the next reaction. The filtrate was cooled to 5C and then incubated for 0.5 hour to obtain a crude product. Used in the next reaction of the product; the crude product was recrystallized from methanol to give 9.5 g of 9,9-bis(4-hydroxyphenyl)indole as a white solid yield 92.8%. The measured melting point is 224.2 to 225.5C, HPLC purity 99.5%.
91%	With N-(3-sulfopropyl)-2-mercaptobenzothiazole p-toluenesulfonate; at 110℃; for 3h;Green chemistry;	Accurately weigh 0.1 mol of anthrone and add it to a 250 mL three-necked flask, followed by0.4 mol of phenol and 0.010 mol of acidic ionic liquid N-(3-sulfopropyl)-2-indenyl The benzothiazole p-toluenesulfonatewas stirred and reacted at 110 C for 3 h.A sample was taken for liquid chromatography analysis, the conversion of anthrone was 100%, andthe selectivity ofbisphenol oxime (9,9-bis(p-hydroxyphenyl)anthracene) was 94% (as shown in Figure 1).The reaction solution was poured into a beaker while hot, and anappropriate amount of 20 C waterwas added to the beaker towash the ionic liquid, and the layer was allowed to stand. The ionic liquid catalyst was distilled off from the aqueous phase under reduced pressure; and90 C hot water was addedto the oily viscoussolid. After thorough mixing, the mixture was allowed to stand for separation, and the aqueous phase was separated from the oily viscous solid phase. The above operation was repeateduntil the hot phase was stirred at 90 C, and the solid phase was no longer viscous.The solid particles and the filtrate were obtained under reduced pressure, and the solid particleswere dried to obtain a bisphenol hydrazine product.The filtrate which was suction-filtered under reduced pressure was distilled under reduced pressure to obtain phenol, and the phenol recoverywas 80%.The solid crude product was recrystallized from methylene chloride to give purified bisphenolphthalein in a yield of 91%, and the purity of the bisphenol oxime wasmore than 99%.
89%	With C10H12NO3S2(1+)*HO4S(1-); at 90℃; for 6h;	Preparation of bisphenolphthalein:Accurately weighedA certain amount of fluorenone, added to a 50 mL three-necked flask, then add the right amount of phenol,Ionic Liquid [(CH2)3SO3HBth][HSO4],At a temperature of 90C,heating,Backflow 6h,After the reaction is over,Dip a suitable amount of reaction solution into CH3OH with a glass rod.Analyzed by liquid chromatography. Pour the reaction solution into the beakerAdd an appropriate amount of water at 20C in the beaker to wash it.Stably layered,The upper layer is water phase,The lower layer is an oily viscous solid.Separating the aqueous phase from the oily viscous solid phase,The aqueous phase contains an ionic liquid catalyst and a small amount of phenol,Pending;Add 90C hot water to the viscous solidStir with a glass rod,Stably layered,The upper layer is water phase,The lower layer is still an oily viscous solid,Separating the aqueous phase from the oily viscous solid phase,Repeat the above operation,After adding hot water at 90C, stirThe solid phase is no longer viscous,Solids become granular,Stop the above operation.Decompression,Get solid particles and filtrate,Dry the solid particles,That is,Bisphenol quinone of crude product,The solid yield was 94%.Recrystallization of bisphenolphthalein,The yield of bisphenolphthalein is 89%.Product purity is greater than 99%.
85%	With silica-gel-supported sulfuric acid; 3-mercaptopropionic acid; In toluene; at 30 - 45℃; for 3.5h;Inert atmosphere;	A solid acid H2SO4-SiO2 catalytic preparation of bisphenol fluorene process, the method comprises the following steps: 1) In a 1000 ml three-necked flask equipped with a thermometer, 50 g (0.275 mol) of 9-fluorenone was added under nitrogen atmosphere, phenol (157 g, 1.67 mol), toluene 50 ml, 1 g (0.01 mol) of 3-mercaptopropionic acid was added dropwise, after being completely dissolved by heating to 30 C, 16.6 g (8% wt) of solid acid H2SO4-SiO2 was slowly added, after completion of the dropwise addition, the reaction was carried out at 45 C for 3.5 hours, after completion of the reaction, the solution A was analyzed for bisphenol fluorene content, 96.50% (HPLC detection), the test results shown in Figure 2. 2) Solution A was hot filtered at 45 C to recover the solid acid, the filtrate was distilled to remove toluene, and then 100 ml of boiling water was added to the reaction flask to make two phases. Poured into 250 ml of ice water while vigorously stirred, the precipitated solid was suction filtered, the solid B and filtrate C were obtained. 3) Solid B was dried at 60 C for 2 hours, to obtain 91.5 g of bisphenol fluorene as a white solid powder, yield 98, purity 96.0%; by toluene and methanol mixture solution (V toluene: V methanol = 10: 1) 275 ml recrystallization, filtered, 80 deg. C drying, a white crystalline bisphenol fluorene 80 grams, yield 85%, purity 99.7%;
85%	With methanesulfonic acid; 3-mercaptopropionic acid; In toluene; at 40℃; for 13h;Inert atmosphere;	Under a nitrogen atmosphere, 9-fluorene (138.7 mmol, 25.0 g), phenol (332.5 mmol, 31.29 g) was added to a 500 Ml reaction flask,3-Mercaptopropionic acid (13.8 mmol, 1.47 g) was added and toluene (140.5 g) was added. Methanesulfonic acid (276.7 mmol, 26.6 g) was added to the mixture, the temperature was gradually raised to 40 C, and the mixture was stirred at the same temperature for 13 hours. The reaction mixture was cooled to room temperature and then concentrated to remove toluene, 155.5 g of tetrahydrofuran was added and dissolved by stirring. After confirming dissolution, 198.7 g of methylene chloride was added, and the mixture was washed twice with 150.0 g of purified water, and concentrated to remove the solvent. 175.0 g of methanol was added, and the mixture was heated to reflux for 30 minutes. After cooling to 10 C, the mixture was stirred for 1 hour, filtered and dried to obtain the target compound, 9,9-bis (4-hydroxyphenyl) fluorene (1-1) (yield: 85%).
85%	With methanesulfonic acid; 3-mercaptopropionic acid; In toluene; at 40℃; for 13h;Inert atmosphere;	Under a nitrogen atmosphere, 9-fluorene (138.7 mmol, 25.0 g), phenol (332.5 mmol, 31.29 g)3-mercaptopropionic acid(13.8 mmol, 1.47 g) was added and toluene (140.5 g) was added.To the mixture was added methanesulfonic acid(276.7 mmol, 26.6 g) was added thereto, the temperature was gradually raised to 40 C, and the mixture was stirred at the same temperature for 13 hours.The reaction mixture was cooled to room temperature and then concentrated to remove toluene,155.5 g of tetrahydrofuran was added and dissolved by stirring.After confirming dissolution, 198.7 g of methylene chloride was added, and the mixture was washed twice with 150.0 g of purified water and concentrated to remove the solvent.175.0 g of methanol was added, and the mixture was heated to reflux for 30 minutes. After cooling to 10 C, the mixture was stirred for 1 hour, filtered, and dried to obtain the target compound, 9,9-bis (4-hydroxyphenyl) fluorene (4-1)

Reference： [1]Patent: US4467122,1984,A
[2]Patent: US4467122,1984,A
[3]Patent: CN104693012,2017,B .Location in patent: Paragraph 0029-0038
[4]Patent: CN108863728,2018,A .Location in patent: Paragraph 0034-0037; 0050; 0054; 0055
[5]Patent: CN108570019,2018,A .Location in patent: Paragraph 0060; 0061; 0063; 0065; 0075
[6]Patent: CN107698429,2018,A .Location in patent: Paragraph 0032; 0034
[7]Patent: CN105693475,2016,A .Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035
[8]Patent: KR101692343,2017,B1 .Location in patent: Paragraph 0082; 0083; 0084; 0085
[9]Patent: KR101716647,2017,B1 .Location in patent: Paragraph 0104-0107
[10]Polymer,2012,vol. 53,p. 2001 - 2007
[11]Organic Letters,2006,vol. 8,p. 2787 - 2790

6
[ 80-05-7 ]
[ 383-29-9 ]
[ 3236-71-3 ]
polymer; monomer(s): 4-fluorophenyl sulfone; 9,9-bis(4-hydroxyphenyl)fluorene; 4,4\-isopropylidenediphenol [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 7121 - 7126

7
[ 80-05-7 ]
[ 383-29-9 ]
[ 3236-71-3 ]
polymer; monomer(s): bis(4-fluorophenyl)sulfone; 9,9-bis(4-hydroxyphenyl)fluorene; 2,2-bis(4-hydroxyphenyl)propane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3879 - 3887

8
[ 358-23-6 ]
[ 3236-71-3 ]
[ 218769-04-1 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2017,vol. 55,p. 1984 - 1990
[2]Macromolecules,2005,vol. 38,p. 4147 - 4156

9
[ 92-88-6 ]
[ 383-29-9 ]
[ 3236-71-3 ]
polymer; monomer(s): bis(4-fluorophenyl)sulfone; 9,9-bis(4-hydroxyphenyl)fluorene; 4,4\-dihydroxy-1,1\-biphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3879 - 3887

10
[ 383-29-9 ]
[ 3236-71-3 ]
[ 5613-46-7 ]
polymer; monomer(s): bis(4-fluorophenyl)sulfone; 9,9-bis(4-hydroxyphenyl)fluorene; 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3879 - 3887

11
[ 383-29-9 ]
[ 3236-71-3 ]
polymer; monomer(s): 4-fluorophenyl sulfone; 9,9-bis(4-hydroxyphenyl)fluorene [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 7121 - 7126

12
[ 383-29-9 ]
[ 3236-71-3 ]
polymer; monomer(s): bis(4-fluorophenyl)sulfone; 9,9-(4-hydroxyphenyl)fluorene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3879 - 3887

13
[ 862095-62-3 ]
[ 3236-71-3 ]
polymer, M_n 3.2E₄ Da, PDI 1.8 [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 5844 - 5845

14
[ 3236-71-3 ]
[ 106-89-8 ]
9,9-bis[4-(2,3-epoxypropoxy)phenyl]fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		EXAMPLE 2SYNTHESIS OF 2,2'-(4,4,-(9H-FLUORENE-9,9-DIYL)BIS(4,1-PHENYLENE))BIS(OXY)BIS(METHYLENE)DIOXIRANE (2)Sodium hydride (60% dispersion in mineral oil, 502 mg, 12.5 mmol, 2.2 equiv) was added slowly to a stirred solution of 4,4'-(9-Fluorenylidene)diphenol (2000 mg, 5.70 mmol, 1 equiv, available from Aldrich Chemicals, catalog No. 3236-71-3) in anhydrous dimethyl formamide (20 mL), at room temperature, and the contents were stirred under an atmosphere of argon for 20 min. Racemic epichlorohydrin (1340 , 17.1 mmol, 3.0 equiv) was added via syringe and the mixture was allowed to react at room temperature for 162 h. Then, the reaction was quenched by the addition of a saturated solution of ammonium chloride (10 mL), and the mixture was extracted with ethyl acetate (3 x 20 mL). The organic layer was washed with deionized water (20 mL), was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (eluent: 10% ethyl acetate in hexane to 20% ethyl acetate to 100% dichloromethane) to provide 2 (2.53 g, 96%) as a white solid. H NMR (400 MHz,DMSO-de): delta 7.90 (d, J= 7.6, 2H), 7.38 (t, J= 8.4, 4H), 7.30 (t, J= 7.2, 2H), 7.02 (d, J = 9.2, 4H), 6.84 (d, J = 8.8, 4H), 4.26-4.22 (dd, J = 11.6, 2.4, 2H), 3.79-3.75 (dd, J = 11.6, 6.4, 2H), 3.29-3.25 (m, 2H), 2.81 (t, J = 4.4, 2H), 2.67-2.65 (dd, J= 5.2, 2.8, 2H); 13C NMR (100 MHz, DMSO-d6): delta 156.9, 151.1, 139.3, 137.9, 128.7, 127.8, 127.5, 125.9, 120.5, 114.3, 68.9, 63.6, 49.6, 43.7; HRMS (ESI) (m/z): calc'd for Cs^eC^Na [M+Na]+: 485.1729, found: 485.1741.
90%	With tetramethlyammonium chloride; sodium hydroxide; In water; dimethyl sulfoxide; toluene; at 40 - 100℃; for 1h;Inert atmosphere;	Under a nitrogen atmosphere, 209.0 g of toluene and 53.0 g of DMSO were added to a 1 L reaction flask and the temperature was raised to 40 C. A solution prepared by dissolving 100.0 g (285.3 mmol) of 9-bis [4- (glycidyloxy) phenyl] fluorene (2) and 316.87 g (3.42 mol) of epichlorohydrin dissolved in another reactor was added to the above reaction solution Respectively. On the other hand, 0.344 g (3.1 mmol) of tetramethylammonium chloride, 16 g of purified water and 22.8 g (0.57 mol) of NaOH were added to another reactor and dissolved. The solution was poured into the preceding reaction solution, heated to 100 C and refluxed for 1 hour. After completion of the reaction, the reaction solution was cooled to 40 C. After completion of the reaction, the reaction solution was cooled to 40 C. 60 ml of hexane, 300 ml of methylene chloride and 300 ml of 1N-HCl were added, followed by stirring and separation. The mixture was washed twice with 250 ml of purified water, and the organic layer was concentrated. Methanol (200 ml) was added thereto, followed by stirring for 12 hours. Filtered and dried to obtain 9,9-bis (4-glycidyloxyphenyl) fluorene (1-2) as a target compound yield: 90%.
90%	With tetramethlyammonium chloride; sodium hydroxide; In water; dimethyl sulfoxide; toluene; at 40 - 100℃; for 1h;Inert atmosphere;	Under a nitrogen atmosphere, a 1 L reaction flask was charged with 209.0 g of toluene, 53.0 g of DMSOAnd the temperature was raised to 40 .In the other reactor, 9-bis [4- (glycidyloxy) phenyl] fluorene100.0 g(285.3 mmol),Epichlorohydrin316.87g (3.42mol) was added to the solution, and the solution was injected into the above reaction solution.On the other hand, another reactor was charged with tetramethylammonium chloride(3.1 mmole), purified water (16 g) and NaOH (22.8 g, 0.57 mol) were added and dissolved. The solution was poured into the preceding reaction solution, heated to 100 and refluxed for 1 hour.After completion of the reaction, the reaction solution was cooled to 40 . 60 ml of hexane, 300 ml of methylene chloride and 300 ml of 1N-HCl were added, followed by stirring and separation. Washed twice with 250 ml of purified water, and the organic layer was concentratedMethanol (200 ml) was added thereto, followed by stirring for 12 hours. Filtered and dried to obtain 9,9-bis (4-glycidyloxyphenyl) fluorene (4-2) as a target compound [yield: 90%.

With tert-butylamine hydrobromide; sodium hydroxide; In water; toluene; at 40 - 90℃; for 1h;

[198]To a 3,000 mL three-neck round-bottom flask, 200 g of toluene, 125.4 g of 4,4'-(9-fluorenylidene)diphenol and 78.6 g of epichlorohydrin were added, and heated to 40 with stirring to obtain a solution. 0.1386 g of t-butylammonium bromide and a 50% NaOH aqueous solution (3 eq) were mixed in a vessel and the mixture was slowly added to the resulting solution with stirring.[199]The reaction mixture thus obtained was heated to 90 for 1 hour to remove 4,4'-(9-fluorenylidene)diphenol completely, which was confirmed by HPLC or TLC. The reaction mixture was cooled to 30, and 400 mL of dichloromethane and 300 mL of 1N HCl were added thereto with stirring. Then, the organic layer was separated, washed with 300 mL of distilled water twice or three times, dried over magnesium sulfate, and distilled under a reduced pressure to remove dichloromethane. The resultant was recrystallized using a mixture of dichloromethane and methanol to obtain the title compound, an epoxy resin compound.

Reference： [1]Patent: WO2012/145330,2012,A1 .Location in patent: Page/Page column 125
[2]Patent: KR101692343,2017,B1 .Location in patent: Paragraph 0082; 0083; 0086; 0087
[3]Patent: KR101716647,2017,B1 .Location in patent: Paragraph 0108-0109
[4]Molecules,2006,vol. 11,p. 953 - 958
[5]Patent: WO2017/78271,2017,A1 .Location in patent: Paragraph 197-199

15
[ 956904-39-5 ]
[ 765314-37-2 ]
[ 3236-71-3 ]
polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)-9-silafluorene, 40 spectr.%; 9,9-bis(4-hydroxyphenyl)fluorene, 60 spectr.% [ No CAS ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 1138 - 1139

16
[ 956904-39-5 ]
[ 765314-37-2 ]
[ 3236-71-3 ]
polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)-9-silafluorene, 18 spectr.%; 9,9-bis(4-hydroxyphenyl)fluorene, 82 spectr.% [ No CAS ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 1138 - 1139

17
[ 956904-39-5 ]
[ 765314-37-2 ]
[ 3236-71-3 ]
polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)-9-silafluorene, 65 spectr.%; 9,9-bis(4-hydroxyphenyl)fluorene, 35 spectr.% [ No CAS ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 1138 - 1139

18
[ 765314-37-2 ]
[ 3236-71-3 ]
polymer; monomers: 9,9-dimethyl-2,7-bis(chlorocarbonyl)fluorene; 9,9-bis(4-hydroxyphenyl)fluorene [ No CAS ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 1138 - 1139

19
[ 3236-71-3 ]
[ 110299-18-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1953 - 1956
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2175 - 2178
[2]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1953 - 1956
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2175 - 2178

20
[ 3236-71-3 ]
9,9'-bis[4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl]fluorene [ No CAS ]

Reference： [1]Molecules,2006,vol. 11,p. 953 - 958

21
[ 3236-71-3 ]
[ 59507-08-3 ]

Reference： [1]Revue Roumaine de Chimie,2005,vol. 50,p. 579 - 587

22
[ 3236-71-3 ]
[ 59507-07-2 ]

Reference： [1]Revue Roumaine de Chimie,2005,vol. 50,p. 579 - 587

23
[ 486-25-9 ]
[ 3236-71-3 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1212 - 1218

24
[ 100-66-3 ]
poly[styrene (iodoso diacetate)] [ No CAS ]
[ 3236-71-3 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1212 - 1218

25
[ 3236-71-3 ]
Dimethyl-thiocarbamic acid S-{4-[9-(4-dimethylcarbamoylsulfanyl-phenyl)-9H-fluoren-9-yl]-phenyl} ester [ No CAS ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 15237 - 15246

26
[ 75-21-8 ]
[ 3236-71-3 ]
BPF [ No CAS ]
[ 117344-32-8 ]

Yield	Reaction Conditions	Operation in experiment
2.0%Chromat.; 98.0%Chromat.	anion exchange resin A (Cl-type); In 2-methoxy-ethanol; at 100℃; for 12h;	[0152] Reaction of adding EO to bisphenol fluorene (BPF) was carried out in the similar manner as in Example 1 except for the following. Specifically, into an autoclave, charged were 100 g of BPF, 200 g of ethyleneglycol monomethyl ether (delta=11.4), and 10.0 g of anion exchange resin A (Cl-type dried material), with addition of 31 g of EO. Next, the mixture was reacted in the autoclave at 100 C. for 12 hours. After the reaction, the anion exchange resin A was separated from the reaction solution. [0153] A result of GC analysis on the composition of the reaction solution reveals that the content of BPF-2EO was 97.1%, and the content of BPF-3EO was 2.7%, respectively. No BPF and BPF-1EO were detected. [0154] EXAMPLE 11; After letting the reaction solution obtained in Example 10 stand at 25 C., a white solid was precipitated. The solid was recovered and dried. A result of GC analysis on the composition of the reaction solution reveals that the content of BPF-2EO was 98.0%, and the content of BPF-3EO was 2.0%, respectively. The yield of BPF-2EO was 60%.

Reference： [1]Patent: US2004/181099,2004,A1 .Location in patent: Page 14

27
[ 3236-71-3 ]
[ 128406-10-0 ]

Reference： [1]Patent: JP2005/82564,2005,A .Location in patent: Page/Page column 8-9

28
[ 3236-71-3 ]
[ 403-33-8 ]
[ 848391-87-7 ]

Reference： [1]Patent: JP2005/82564,2005,A .Location in patent: Page/Page column 9

29
[ 451-46-7 ]
[ 3236-71-3 ]
9,9'-bis-[(4-ethoxycarbonyl-phenyl)-oxyphenyl]-fluorene [ No CAS ]

Reference： [1]Patent: WO2004/2934,2004,A1 .Location in patent: Page/Page column 15-16

30
[ 3236-71-3 ]
[ 100-00-5 ]
[ 139265-69-3 ]

Reference： [1]Patent: WO2006/85493,2006,A1 .Location in patent: Page/Page column 8-10
[2]Thermochimica Acta,2013,vol. 564,p. 51 - 58

31
[ 24424-99-5 ]
[ 3236-71-3 ]
[ 469859-71-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 111 Synthesis of 9-[4-(tert-butoxycarbonyloxy)phenyl]-9-[4-hydroxyphenyl]fluorene (Compound 111) 9-[4-(tert-butoxycarbonyloxy)phenyl]-9-[4-hydroxyphenyl]fluorene was obtained in the same manner as in the Example 20, except for using 1/2 mole of di-tert-butyl dicarbonate relative to 1 mole of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong> and being purified with a silica gel column chromatography (eluent: hexane/ethyl acetate=7/3). 1H-NMR(CDCl3) ppm: 1.55(s, 9H, tert-Bu), 6.67(d, 2H, C6H4), 7.00(d, 2H, C6H4), 7.06(d, 2H, C6H4), 7.19(d, 2H, C6H4), 7.22-7.39(m, 6H, C13H8), 7.75(d, 2H, C13H8).

Reference： [1]Patent: US2003/211421,2003,A1

32
[ 3236-71-3 ]
[ 469858-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Example 20 Synthesis of 9,9-bis[4-(tert-butoxycarbonyloxy)phenyl]fluorene (Compound 20) 9,9-bis[4-(tert-butoxycarbonyloxy)phenyl]fluorene was obtained in the same manner as in the Example 2, except for using <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong> and toluene as the recrystallization solvent in lieu of 4-isopropylphenol and methanol, respectively. 1H-NMR(CDCl3) ppm: 1.55(s, 18H, tert-Bu), 7.03(d, 4H, C6H4), 7.27(d, 4H, C6H4), 7.15-7.41(m, 6H, C13H8), 7.76(d, 2H, C13H8).

Reference： [1]Patent: US2003/211421,2003,A1

33
3-fluoro-6-nitrobenzyloxybenzene [ No CAS ]
[ 3236-71-3 ]
[ 359820-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; Petroleum ether;	EXAMPLE 1 Preparation of 9,9-bis(4-[(3-benzyloxy-4-nitro)phenoxy]phenyl)fluorene 100.0 g of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong> (0.285 mol) and 142.5 g of 3-fluoro-6-nitrobenzyloxybenzene (0.576 mol) are dissolved in 1050 ml of dimethylformamide. 200.0 g of K2CO3 (1.447 mol) is then added and the mixture stirred continuously for 3 hours at 135 C. At the end of the reaction the mixture is cooled to room temperature and poured with stirring into 2.5 l of ice water. The yellow solid which precipitates is filtered off using a Buechner funnel, washed once with dilute acetic acid and once with water and then dried in a vacuum chamber under nitrogen at 50 C./50 mbar. For purification the crude product is dissolved in 800 ml of tetrahydrofuran at the boiling point and 800 ml of petroleum ether (bp 60-80 C.) is added. For crystallization the solution is kept at 4 C. for 12 hours and the white solid filtered off using a Buechner funnel and dried in the vacuum cabinet under nitrogen at 50 C./50 mbar. Yield: 211.0 g. Characterization: Mass spectrum: molecular ion at 804

Reference： [1]Patent: US2002/10370,2002,A1

34
3-fluoro-6-nitrobenzyloxybenzene [ No CAS ]
[ 3236-71-3 ]
[ 359820-19-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; Petroleum ether;	EXAMPLE 3 Preparation of 9-(4-[(3-benzyloxy-4-nitro)phenoxy]phenyl)-9-(4-hydroxyphenyl)fluorene 50.0 g of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong> (0.143 mol) and 35.28 9 of 3-fluoro-6-nitrobenzyloxybenzene (0.143 mol) are dissolved in 550 ml of dimethylformamide. 100.0 g of K2CO3 (0.724 mol) is then added and the mixture is stirred at 120 C. for 5 hours. At the end of the reaction the mixture is cooled to room temperature and poured with stirring into 1.0 l of ice water. The yellow solid which precipitates is filtered off using a Buechner funnel, washed once with dilute acetic acid and once with water and then dried in a vacuum chamber under nitrogen at 50 C./50 mbar. The crude product is purified by recrystallization according to Example 1 with 350 ml of tetrahydrofuran and 350 ml of petroleum ether. Yield: 73.51 g. Characterization: Mass spectrum: molecular ion at 577

Reference： [1]Patent: US2002/10370,2002,A1

35
[ 486-25-9 ]
[ 107-96-0 ]
[ 108-95-2 ]
[ 3236-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;	Example 1 9,9-bis-(4-hydroxyphenyl)fluorene (Compound 1) 9-Fluorenone (18.0 g, 99 mmol), phenol (37.6 g, 400 mmol) and 3-mercaptopropionic acid (0.8 g, 7 mmol) were heated to 60 C. under nitrogen. When all the solid had melted, dry hydrogen chloride gas was bubbled through the solution for 2 hours. The mixture was then heated at 80 C. for four hours. A solid formed, which was isolated by filtration. Excess phenol was distilled off under vacuum. The resulting solid was then recrystallized from toluene/hexane to give the title compound (26.0 g) as a solid. M.P. 215 C.

Reference： [1]Patent: US5447960,1995,A

36
[ 124-73-2 ]
[ 3236-71-3 ]
9,9-Bis(4'-[Trifluorovinyloxy]Phenyl)Fluorene [ No CAS ]
9,9-bis(4'-[2"-bromotetrafluoroethoxy]phenyl)fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium hydroxide; nitrogen; In hexane; dimethyl sulfoxide; toluene;	EXAMPLE 3 Preparation and Polymerization of 9,9-Bis(4'-[Trifluorovinyloxy]Phenyl)Fluorene Into a 2 liter 5-necked round bottom flask fitted with a mechanical stirrer, Dean-Stark trap topped with a nitrogen padded reflux condenser and a thermocouple attached to a temperature controller, are placed DMSO (650 ml) and toluene (200 ml). While the stirred solution is purged with nitrogen, 9,9-bis(4'-hydroxyphenyl)fluorene (200.0 g, 0.57 mole) is added to the flask. While purging with nitrogen continues, potassium hydroxide (85% pellets, 77.5 g, 1.17 mole) is added all at once, and the mixture is heated to 100 C. with constant stirring. After two hours, the temperature is increased until the solution begins to reflux (130 C.). Water is removed by azeotropic distillation for 24 hours. The Dean-Stark trap is replaced by a Soxhlet extractor containing anhydrous sodium sulfate, and the toluene is refluxed through the Soxhlet for 5 hours. A small amount of toluene (60 ml) is then removed by simple distillation. Then the reactor is cooled to 35 C. Addition of 1,2-dibromotetrafluoroethane (315 g, 1.21 mole) via dropping addition funnel is then maintained at a rate that keeps the reaction temperature at 35-38 C. When the addition is complete, the mixture is heated at 50 C. for 8 hours, then cooled to room temperature with constant stirring. The mixture is filtered, and the precipitate is washed twice with acetone. The filtrates are combined and evaporated thoroughly. The residue from the evaporation is washed with water to remove residual potassium bromide (KBr). After the residue is air dried for 24 hours, it is purified by column chromatography (on neutral alumina, using hexane eluent) to provide as product, 9,9-bis(4'-[2"-bromotetrafluoroethoxy]phenyl)fluorene (331.4 g, 0.468 mole, 82% yield), melting point 157-158 C. The LC/MS spectrum has peaks at: m/e: 710 (53 0%); 709 (34.0%): 708 (100.0%); 707 (23.3%); 706 (49.8%): 513 (28.4%); 511 (28.5%); 438 (12.8%): 437 (52.4%): 436 (14.7%): 435 (55.8%): 355 (15.7%): 290 (33.9)%: 289 (19.5%); 239 (35.9%): 228 (36.2%); 227 (38.9%); 226 (47.3%): 202 (27.7%); 157 (47.2%); 131 (27.6%): 129 (23.1%).

Reference： [1]Patent: US5023380,1991,A

37
[ 486-25-9 ]
[ 108-95-2 ]
[ 620-92-8 ]
[ 3236-71-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride; In Zinc chloride; water; isopropyl alcohol;	EXAMPLE 3 9,9-bis-(4-hydroxyphenyl)-fluorene 30 moles of phenol containing 9% by weight of water were stirred in an autoclave and then 2 moles of zinc chloride and 10 moles of fluorenone were dissolved therein. Then, 10 moles of gaseous hydrogen chloride were added to the stirred mixture and the mixture was reacted at 80 C. for one hour and then at 70 C. for 3 hours. The reaction mixture was then dissolved in 5 liters of isopropanol at 60 C. and the solution was then poured with vigorous stirring into a ten-fold volume of water whereby the resulting bisphenol precipitated as 3.4 kg (97% yield) of the product in the form of a yellow product.
81%	In Zinc chloride; water; isopropyl alcohol;	EXAMPLE 6 9,9-bis-(4-hydroxyphenyl)-fluorene 15 moles of phenol containing 9% by weight of water were stirred in an autoclave at 50 C. and then one mole of zinc chloride and 5 moles of fluorenone were dissolved therein. The mixture was saturated with gaseous hydrogen chloride and the mixture was reacted at room temperature for 2 days. The mixture was dissolved in 2.5 liters of isopropanol at 60 C. and the solution was poured with vigorous stirring into a 10 fold volume of water to obtain 1.6 kg (92% yield) of the desired bisphenol in the form of a light yellow product. Crystallization from toluene gave an 81% yield of crystalline product with a purity equal to that of Example 5.

Reference： [1]Patent: US4467122,1984,A
[2]Patent: US4467122,1984,A

38
[ 3236-71-3 ]
[ 88-73-3 ]
9,9-bis-[4-(p-aminophenoxy)phenyl]fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium-carbon; In N-methyl-acetamide; toluene;	[Example 2] To a two-liter four-neck flask equipped with a stirrer, a thermometer, a Dean-Stalk trap, and a reflux condenser, there were poured 150 g (0.428 mole) of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong>, 149 g (0.946 mole) of 2-chloronitrobenzene, 130 g (0.943 mole) of potassium carbonate, 50 g of toluene, and 700 g of dimethylformamide. The same procedure to that of Example 1 was applied to obtain 246 g of corresponding aromatic dinitro compound. The yield of the obtained dinitro compound was 94.2% on the basis of 9,9-bis (4-hydroxyphenyl)fluorene. A 150 g (0.246 mole) aliquot of thus obtained dinitro compound was reduced using 7.5 g of palladium-carbon (supporting the palladium by 5%) and 550 g of dimethylformamide by the same procedure to that in Example 1, thus obtained 124 g of 9,9-bis[4-(2-aminophenoxy)phenyl]fluorene.

Reference： [1]Patent: EP1803705,2007,A1

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 6 Polymerizing the monomer of Example 5 (Compound (7)) with 9,9-bis(4-hydroxyphenyl)fluorene to provide a polyquinoline polymer of the following structure: A three-necked, 2 L round-bottomed flask equipped with a mechanical stirrer, a Dean-Stark trap fitted with a condenser and a nitrogen inlet valve, and a thermometer was charged with Compound (7) provided in Example 5 (114.75 g, 0.19225 mol, 1.03 eq), 9,9-bis(4-hydroxyphenyl)fluorene (66.0472 g, 0.18848 mol, 1.00 eq), potassium carbonate (39.1 g, 0.28 mol, 1.5 eq), NMP (705 mL), and toluene (421 mL). The reaction mixture was heated to reflux under nitrogen (15 h). The toluene was removed through the Dean Stark trap, and the reaction was further heated at 200C (12 h). The reaction mixture was diluted with NMP and cooled to room temperature. The polymer was coagulated by slowly pouring the resulting polymer solution into acetone (ca. three volumes). The solid was collected by filtration, dissolved in NMP, and coagulated in water (ca. three volumes). The solid was collected and dried under vacuum at 130C (12 h). Yield 170 g, 99%; Mn = 46,900 by GPC relative to polystyrene standards. Polyquinoline 11 has a Tg of about 306C.

40
[ 50-00-0 ]
[ 3236-71-3 ]
[ 124-40-3 ]
[ 912474-44-3 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2016,vol. 54,p. 935 - 944
[2]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3358 - 3366

41
[ 50-00-0 ]
[ 3236-71-3 ]
[ 124-40-3 ]
[ 912474-64-7 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2016,vol. 54,p. 935 - 944
[2]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3358 - 3366

42
ClCOC₆H₄CB₁₀H₁₀CC₆H₄COCl [ No CAS ]
[ 3236-71-3 ]
OCC₆H₄CB₁₀H₁₀CC₆H₄COOC₆H₄(C₁₃H₈)C₆H₄O [ No CAS ]

Reference： [1]Izvestiya Akademii Nauk Kazakhskoi SSR, Seriya Khimicheskaya,1973,vol. 23,p. 78 - 81
C. A.,1973,vol. 79,p. 19329

43
[ 3236-71-3 ]
[ 3132-64-7 ]
9,9-bis[4-(2,3-epoxypropoxy)phenyl]fluorene [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals,2009,vol. 498,p. 235 - 241

44
[ 3236-71-3 ]
[ 36530-06-0 ]
(B(N₆C₂₄H₁₂))2O₂C₆H₄C(C₁₂H₈)C₆H₄ [ No CAS ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 3915 - 3922
[2]Dalton Transactions,2010,vol. 39,p. 3915 - 3922

45
[ 3236-71-3 ]
[ 74-88-4 ]
[ 117766-40-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In N,N-dimethyl-formamide; at 10℃;	To a 500 mL four-necked flask, 35.0 g (0.10 mole) of 9,9-bis(4-hydroxyphenyl)-9H-fluorene and 300 mL of dimethylformamide were fed, and the resulting mixture was allowed to dissolve, followed by addition of 63.6 g (0.46 mole) of potassium carbonate to the resulting solution. The resulting mixture was cooled to 10C and 31.2 g (0.22 mole) of methyl iodide was added thereto dropwise, followed by stirring the mixture for 6 hours. To this mixture, 500 mL of methyl isobutyl ketone was fed, and the resulting mixture was washed 3 times with 400 mL of water, followed by concentrating thereof under reduced pressure to obtain a crude product. To this crude product, 300 mL of methyl isobutyl ketone was added and the crude product was allowed to dissolve under heat, followed by addition of 300 mL of methanol, collection of yielded crystals by filtration and drying thereof to obtain 29.7 g of 9,9-bis(4-methoxyphenyl)-9H-fluorene. The yield was 79%.

Reference： [1]Patent: EP2186799,2010,A1 .Location in patent: Page/Page column 22; 23

46
[ 3236-71-3 ]
[ 395-25-5 ]
[ 33454-82-9 ]
trifluoromethanesulfonate [9,9-bis(4-hydoxyphenyl)-9H-fluorene-2-yl]bis(4-fluorophenyl)sulfonium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		To a 100 mL four-necked flask, 360 g (3.75 moles) of methanesulfonate and 35.5 g (0.25 mole) of phosphorus pentoxide were fed, and the atmosphere was replaced with nitrogen, followed by heating the mixture at 100C to dissolve it. After cooling thereof, 59.6 g (0.25 mole) of bis(4-fluorophenyl)sulfoxide and 87.5 g (0.25 mole) of 9,9-bis(4-hydroxyphenyl)-9H-fluorene were fed to the solution, and the resulting mixture was allowed to react by stirring at 50C for 2 hours. Subsequently, 2000 mL of ice water and 1000 mL of methanol were mixed with each other and the above reaction solution was added to this mixture. To this, 1000 mL of methylene chloride, 500 mL of water and 40.6 g (0.26 mole) of lithium trifluoromethanesulfonate were added, and the resulting mixture was stirred for 2 hours. The methylene chloride layer was washed 3 times with 500 mL of water and concentrated under reduced pressure to obtain white solids, which was then subjected to a silica gel chromatography. Fractions containing the desired products were collected and concentrated under reduced pressure to obtain 54.1 g of trifluoromethanesulfonate[9,9-bis(4-hydoxyphenyl)-9H-fluorene-2-yl]bis(4-fluorophenyl)sulfonium. The yield was 30%.

Reference： [1]Patent: EP2186799,2010,A1 .Location in patent: Page/Page column 17

47
[ 3236-71-3 ]
[ 1774-34-1 ]
[ 33454-82-9 ]
[ 1112460-26-0 ]

Yield	Reaction Conditions	Operation in experiment
23%		To a 3L three-necked flask, 1441 g (15 moles) of methanesulfonate and 141.9 g (1 mole) of phosphorus pentoxide were fed, and the atmosphere was replaced with nitrogen, followed by heating the mixture at 100C to dissolve it. After cooling thereof, 234 g (1 mole) of bis(hydroxyphenyl)sulfoxide and 350g (1 mole) of 9,9-bis(4-hydroxyphenyl)-9H-fluorene were added thereto, and the resulting mixture was allowed to react at 15C for 2 hours. Subsequently, 5000 g of ice water and 2500 g of methanol were mixed with each other and the above reaction solution was added to this mixture. Precipitated solids were collected by filtration, and 4000 g of methyl isobutyl ketone and 3000 g of water were added thereto, followed by stirring the resulting mixture. To this mixture, 158 g (1.01 moles) lithium trifluoromethanesulfonate was added, and the resulting mixture was stirred for 2 hours. The methyl isobutyl ketone layer was washed 3 times with 3000 g of water and concentrated under reduced pressure to obtain 587 g of white solids. These were subjected to a silica gel chromatography and fractions containing the desired product were recovered, followed by concentration thereof under reduced pressure to obtain white solids. To these, 2000 g of water and 2000 g of methanol were added, and the resulting mixture was heated and dissolved, followed by cooling the solution slowly to allow colorless crystals to precipitate slowly. The precipitated crystals were filtered. These manipulations were repeated 3 times and the resulting crystals were dried to obtain the compound No. 1. The yielded amount was 164 g and the yield was 23%.

Reference： [1]Patent: EP2186799,2010,A1 .Location in patent: Page/Page column 14; 15

48
[ 872864-91-0 ]
[ 3236-71-3 ]
[ 919079-70-2 ]

Yield	Reaction Conditions	Operation in experiment
85%		A 5-L three-necked flas was fitted with an argon inlet, mechanical stirrer and a thermometer, and was charged with isopropanol (1.6 L), dimethylformamide (600 mL) and potassium tert-butoxide (214 g). The reaction mixture was stirred at 50 C. for 10 minutes. 4-4'-(9-fluorenylidene)diphenol (334 g) was added to the reaction mixture; the temperature was raised to 70 C.; and the reaction mixture was stirred for 30 minutes, until the 4-4'-(9-fluorenylidene)diphenol was dissolved. The reaction mixture was then heated to 100 C. to rapidly distill off the isopropanol (boiling point 82 C.). Approximately 1 L of isopropanol was removed by this distillation.An additional amount of dimethylformamide (1.4 L) was added to the reaction flask; the temperature was set to 90 C.; and chloropropylmethyl-diisopropoxysilane (477 g) was added. The reaction mixture was stirred at 100 C. for one hour, and then cooled to room temperature.A mixture of cyclohexane (2 L) and water (100 mL) was added to the room temperature reaction mixture. The mixture was stirred for several minutes, and then stirring was stopped. The layers were allowed to separate. The cyclohexane layer was decanted into a 6-L separatory funnel and washed twice with 1 L of 50% brine solution. The organic layer was removed, dried over magnesium sulfate and filtered through silica gel (600 g), which was washed with 2% ethyl acetate in cyclohexane (1 L). The solvent was collected and concentrated under reduced pressure to give a colorless oil. The compound was purified by Kugelrohr distillation at 180 C. for 2 hours to remove unreacted chloropropylmethyldiisopropoxysilane. The yield of compound (I-6) was 612 g (85%). The desired structure of the product was confirmed by 1H NMR spectroscopy, high performance liquid chromatography and gel permeation chromatography.

Reference： [1]Patent: US7803959,2010,B2 .Location in patent: Page/Page column 24-25

49
[ 515136-37-5 ]
[ 3236-71-3 ]
[ 919079-70-2 ]

Yield	Reaction Conditions	Operation in experiment
75%		4,4-(9-Fluorenylidene)diphenol (17.5 g, mole) was dissolved in isopropanol (70 mL) in a 250 mL round-bottomed flask. To the solution was added a solution of 20 wt % of potassium isopropoxide in isopropanol (49 g) through a dropping funnel. After addition, the solution was stirred at room temperature for 3 hours and the excess isopropanol was removed by rotary evaporation. The remaining solid was dissolved in dimethylformamide (DMF) (mL). To the solution was added iodopropyldiisoproxymethylsilane (36 g) and the temperature was maintained at about 70 C. for an hour, then cooled to 25 C. Potassium iodide (30 g) was added into the solution and it was stirred for about an hour. Cyclohexane (200 mL) was added to extract the product. The cyclohexane layer was collected and washed with deionized water and brine, and dried over sodium sulfate. The excess cyclohexane was removed by rotary evaporation and the final product was purified by distillation under reduced pressure. The yield of compound (I-6) was 28.2 g (75%). The desired structure of the product was confirmed by 1H NMR spectroscopy.

Reference： [1]Patent: US7795462,2010,B2 .Location in patent: Page/Page column 28

50
[ 3236-71-3 ]
[ 619-72-7 ]
C₃₉H₂₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.3%		[Example 1] ; To a two-liter four-neck flask equipped with a stirrer, a thermometer, a Dean-Stalk trap, and a reflux condenser, there were poured 74.7 g (0.213 mole) of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong>, 29.9 g (0.533 mole) of potassium hydroxide, 50 g of toluene, and 790 g of dimethylformamide. While agitating the contents and keeping the system in a nitrogen atmosphere, the system was heated to 110C, thus the generated water was distilled out as an azeotrope with toluene. After completing the water distillation, the temperature of the system was lowered to 100C. A 79.0 g (0.533 mole) of 4-nitrobenzonitrile was charged into the flask to execute reaction at the temperature for 3 hours. After completing the reaction, the reaction product mixture was cooled to room temperature, which was then charged into a 1500 g of 5% hydrochloric acid solution. The deposited crystals were collected by filtration. Thus collected crude crystals were rinsed with 1000 g of water, followed by filtering to remove the residual inorganic salt. The crystals were again rinsed with water and filtered. The crystals were then rinsed with 500 g of methanol and filtered. After repeated the methanol-rinsing and drying once more, the crystals were dried to obtain 104 g of dinitrile compound. The yield of the dinitrile compound was 88.3% on the basis of <strong>[3236-71-3]9,9-bis(4-hydroxyphenyl)fluorene</strong>.

Reference： [1]Patent: EP1834943,2007,A1 .Location in patent: Page/Page column 5-6

51
[ 486-25-9 ]
[ 108-95-2 ]
9,9-bis(hydroxyphenyl)fluorene [ No CAS ]
[ 3236-71-3 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 1837 - 1838
[2]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 1837 - 1838

52
[ 3236-71-3 ]
[ 51762-67-5 ]
[ 301212-04-4 ]

Reference： [1]Polyhedron,2011,vol. 30,p. 522 - 528
[2]Journal of Porphyrins and Phthalocyanines,2012,vol. 16,p. 826 - 832

53
[ 50-00-0 ]
[ 617-89-0 ]
[ 3236-71-3 ]
[ 1245796-76-2 ]

Reference： [1]Thermochimica Acta,2011,vol. 515,p. 32 - 37
[2]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 4020 - 4026

54
[ 3236-71-3 ]
[ 507219-58-1 ]
[ 1403963-48-3 ]