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[ CAS No. 14814-17-6 ]

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2D
Chemical Structure| 14814-17-6
Chemical Structure| 14814-17-6
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Product Details of [ 14814-17-6 ]

CAS No. :14814-17-6MDL No. :MFCD00623913
Formula : C15H14O3 Boiling Point : 421.0±25.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :242.27Pubchem ID :3090643
Synonyms :

Computed Properties of [ 14814-17-6 ]

TPSA : 46.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.13 Rotatable Bond Count : 5

Safety of [ 14814-17-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14814-17-6 ]

  • Upstream synthesis route of [ 14814-17-6 ]
  • Downstream synthetic route of [ 14814-17-6 ]

[ 14814-17-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 75-21-8 ]
  • [ 1137-42-4 ]
  • [ 14814-17-6 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With potassium hydroxide In diethylene glycol diethyl ether for 0.5 h;
Stage #2: at 120℃; for 1 h;
Stage #3: With hydrogenchloride In diethylene glycol diethyl ether; water
I a) Ethylene glycol p-benzophenone ether; In a laboratory autoclave having a capacity of 2 L there were placed 520 g of diethylene glycol diethyl ether, 286 g of p-hydroxybenzophenone (>98 wt percent), and 0.8 g of powdered potassium hydroxide. A pressure test was then carried out for 30 minutes using dry nitrogen. Following pressure let-down to atmospheric pressure and heating of the reaction mixture under a blanket of nitrogen to 120° C., 95.4 g of ethylene oxide were continuously forced in to give a maximum internal pressure of 4 bar over a period of 1 h. On completion of gassing with ethylene oxide, the reaction mixture was allowed to react, until the pressure remained constant for at least 30 minutes. The reaction mixture was discharged from the autoclave in the hot state, neutralized with 5 wt percent strength aqueous hydrochloric acid, and poured into 2 L of ice water, and the reaction product was caused to crystallize by constant agitation. The resulting solid matter was filtered off in vacuo, washed with ice water and dried in vacuo (40° C., 10 mbar absolute). The resulting filtrate was concentrated in a rotary film evaporator to 20percent of its volume, the precipitated product filtered off in vacuo, washed with ice water and likewise dried in vacuo. The total yield was 82percent of theory.
Reference: [1] Patent: US2004/249186, 2004, A1, . Location in patent: Page 7
  • 2
  • [ 1137-42-4 ]
  • [ 540-51-2 ]
  • [ 14814-17-6 ]
Reference: [1] Soft Matter, 2013, vol. 9, # 3, p. 929 - 937
[2] Advanced Functional Materials, 2018, vol. 28, # 11,
[3] Macromolecules, 2010, vol. 43, # 1, p. 249 - 261
[4] RSC Advances, 2018, vol. 8, # 13, p. 6798 - 6804
[5] Patent: US2018/50983, 2018, A1, . Location in patent: Paragraph 0670; 0671; 0672
  • 3
  • [ 1137-42-4 ]
  • [ 107-07-3 ]
  • [ 14814-17-6 ]
YieldReaction ConditionsOperation in experiment
21% With potassium carbonate; sodium iodide In acetoneHeating / reflux Step 1: {4-[(2-Hydroxyethyl)oxy]phenyl}(phenyl)methanone (5)To a solution of 4-hydroxybenzophenone (6.0 g, 29.7 mmol) in acetone (50 mL) were added K2CO3 (12.3 g, 89.0 mmol) and 2-chloroethanol (4.0 mL, 59.3 mmol), followed by addition of NaI (4.50 g, 29.7 mmol). The reaction mixture was refluxed under nitrogen overnight. The mixture was cooled to room temperature. The white solid was filtered off and washed with acetone (100 mL). The filtrate was concentrated to a brown oil residue with some white solid. EtOAc (200 mL) was added, the white solid was filtered off and then washed with 50 mL of EtOAc. The filtrate was washed with 1 N NaOH, water, brine and dried over Na2SO4. Concentration afforded a pale yellow oil which was further purified by chromatography on a silica gel column eluted with a gradient from hexanes to 60percent EtOAc:hexanes to give 5 as a white solid (1.52 g, 21percent). 1H NMR (400 MHz, CDCl3): δ 4.00-4.05 (m, 2H), 4.15-4.20 (m, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.45-7.50 (m, 2H), 7.55-7.60 (m, 1H), 7.75 (d, J=7.1 Hz, 2H), 7.83 (d, J=8.8 Hz, 2H).
Reference: [1] Patent: US2008/167360, 2008, A1, . Location in patent: Page/Page column 19
[2] Patent: US2182786, 1938, ,
[3] Patent: WO2010/65355, 2010, A1, . Location in patent: Page/Page column 23
  • 4
  • [ 96-49-1 ]
  • [ 1137-42-4 ]
  • [ 14814-17-6 ]
YieldReaction ConditionsOperation in experiment
95% With sodium iodide In toluene at 60℃; for 1.5 h; Reflux 4-hydroxybenzophenone (262 g, 1.32 mol)NaI (6.5 g, 0.043 mol),Ethylene carbonate (125 g, 1.42 mol) andToluene (10 mL) were added to a 2000 mL three-necked flask,Raise the temperature until the system is clear.Continue to raise the temperature to the reaction system was refluxed for 1.5h,After the TLC test reaction is completed, the heating is stopped,Cooled to 60 ° C.To the reaction system was added water and ethyl acetate,extraction,The organic phase was dried over anhydrous sodium sulfate,Concentrated to give 304 g of a pale yellow solid,Yield 95percent.
94% With sodium iodide In toluene at 99 - 176℃; for 0.5 h; A mixture of ethylene carbonate (124.6 g; 1.07 eq.), sodium iodide (6.3 g; 0.03 eq.), 4-hydroxybenzophenone (262 g; 1 eq.) and toluene (8.1 g) was heated. At99°C a clear solution was obtained. The reaction mixture was heated with reflux condenser to 176°C over one hour, during which gas evolution occurred. After an additional 1/2 hour at 176°C, the reaction mixture was cooled to 122°C and toluene (350 g) and water (24 g) was added. The lower phase was cut and discarded. More water (14 g) was added and the lower phase was again cut and discarded. Water and toluene (95 g in total) was azeotropically removed, reaching a boiling point of 11 1 °C. More toluene (1 14 g) was added and the product was isolated by filtration at 8°C. In total, 302 g of 4-(2-hydroxyethoxy)benzophenone (94percent) was obtained after drying as white crystals (99.8 percent chromatographic purity).
Reference: [1] Patent: CN104788300, 2017, B, . Location in patent: Paragraph 0038; 0039; 0040;
[2] Patent: WO2011/89385, 2011, A1, . Location in patent: Page/Page column 23
[3] Patent: US4625048, 1986, A,
  • 5
  • [ 335591-82-7 ]
  • [ 14814-17-6 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 11, p. 2695 - 2696
  • 6
  • [ 191332-05-5 ]
  • [ 14814-17-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2314 - 2322
  • 7
  • [ 75230-42-1 ]
  • [ 14814-17-6 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 6, p. 1826 - 1830
[2] Patent: US4861916, 1989, A,
  • 8
  • [ 1892-43-9 ]
  • [ 100-47-0 ]
  • [ 14814-17-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1999, vol. 590, # 1, p. 63 - 70
  • 9
  • [ 34743-88-9 ]
  • [ 100-47-0 ]
  • [ 14814-17-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1999, vol. 590, # 1, p. 63 - 70
  • 10
  • [ 1137-42-4 ]
  • [ 14814-17-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2314 - 2322
  • 11
  • [ 6192-44-5 ]
  • [ 14814-17-6 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 6, p. 1826 - 1830
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