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CAS No. : | 947-19-3 | MDL No. : | MFCD00059561 |
Formula : | C13H16O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QNODIIQQMGDSEF-UHFFFAOYSA-N |
M.W : | 204.26 | Pubchem ID : | 70355 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With tetra(n-butyl)ammonium hydroxide; In water; 1,2-dichloro-ethane; at 35℃; for 1.5h; | 1-chlorocyclohexyl phenyl ketone(44.5g, 0.2mol),100mLDichloroethane is added to the reaction vessel,Stir well and slowly heat to 35 C.25% aqueous solution of tetrabutylammonium hydroxide (249.1 g, 0.24 mol) was added dropwise, and the reaction was kept under stirring for 1.5 h.The reaction is carried out under the detection of TLC or GC. After the reaction is completed,The heating and stirring were stopped, the layer was allowed to stand, the organic phase was separated, the aqueous phase was recovered, and the organic phase was washed with water. Then, the hexane was desolvated and recovered, and 80 mL of petroleum ether was added for recrystallization to obtain a white glossy crystal of 38.0 g (Y=93). %), GC content 99.2%, |
73.12 g | With sodium hydroxide; at 57 - 60℃; for 5h; | (A) 85.8 g (content 92%, 0.42 mol), 75 g 1,1-dichloroethane, 0.5 g L-potassium molecular sieve and 300 g (23%) hydrochloric acid aqueous solution (B) were placed in a 500 ml four-necked flask equipped with a stirrer. the temperature was raised to about 45 C, and 140 g of 30% hydrogen peroxide was added dropwise. The reaction was maintained at 45-50 C. The reaction was followed by chromatography, and the temperature was kept at 50 C for 1 hour, After the end of the reaction, the temperature was controlled to 57-60 C, 33% sodium hydroxide solution was slowly added dropwise for 4 hours. After the addition was completed, the temperature was maintained at 57-60 C for 5 hours. After the reaction, the mixture was allowed to stand for stratification, and the lower organic phase was separated. After cooling, the crystals were cooled to give a crude product (yield: 84 g), and then recrystallized from petroleum ether to give 73.12 g white crystals (content: 99.58 %. 0.356 mol). The molar yield was 84.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Of particular interest are molecular complex compounds comprising ... bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; bis(2,4,6-trimethylbenzoyl)(2-methylpropyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2-methylpropyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; bis(2,6-dimethoxybenzoyl)(2-methylpropyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone and bis(2,6-dimethoxybenzoyl)(2-methylpropyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone. | ||
Of particular interest are molecular complex compounds comprising ... 2,4,6-trimethylbenzoyldiphenylphosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; bis(2,4,6-trimethylbenzoyl)(4-ethoxyphenyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2,4-dihexyloxyphenyl)phosphine oxide and alpha-hydroxy-cyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; bis(2,4,6-trimethylbenzoyl)(2-methylpropyl)phosphine oxide and alpha-hydroxycyclohexyl phenyl ketone; bis(2,4,6-trimethylbenzoyl)(2-methylpropyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropanone; ... | ||
benzophenone derivatives, e.g., benzophenone, Michler's ketone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 2-chlorobenzophenone, 4-bromobenzophenone or 2-carboxybenzophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexylphenylketone, alpha-hydroxy-2-methylphenylpropane, 1-hydroxy-1-methylethyl-(p-isopropylphenyl)ketone, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tetra(n-butyl)ammonium hydroxide; In water; 1,2-dichloro-ethane; at 35℃; for 1.5h; | 1-bromocyclohexyl phenyl ketone(53.4g, 0.2mol),120 mL of dichloroethane was added to the reaction vessel,Stir well, slowly heat to 35 C, add 25% aqueous solution of tetrabutylammonium hydroxide (249.1 g, 0.24 mol), drop 1.5h,The reaction is incubated under stirring, and the reaction is reacted under TLC or GC detection.After the reaction is completed, the heating and stirring are stopped, and the layering is allowed to stand.The organic phase is separated, the aqueous phase is recovered, and the organic phase is washed with water.Then desolvently recovering n-hexane,Recrystallization was carried out by adding 80 mL of petroleum ether to obtain white glossy crystals of 36.7 g (Y = 90%), GC content: 99.2%. |
59% | With sodium hydroxide;N-benzyl-N,N,N-triethylammonium chloride; at 80℃; for 1h; | 6.6 g of 1-bromo-cyclohexyl-phenylketone obtained with Method G (24.7mmoles), were dispersed in 6g of NaOH 30% and heated to 8O0C; lOOmg of benzyl- triethylammonium chloride were added in two portions, and the mixture was stirred at 8O0C for one hour. The organic phase was separated and washed warm with 10 ml of water set a pH 3 with concentrated HCI. The organic phase crystallized from petroleum ether 40-65C obtaining 3g of a whitish solid (59%), mp 45-46C. Hl NMR(300MHz, CDCb): delta: 7.97-8.07 (d,2H); 7.40-7.60 (m,3H); 3.45 (s, I H); 1.97-2.12 (m,2H); 1 .60-1.87 (m,7H); 1 .25-1.45 (m,l H). |
59% | c) Hydroxylation Synthesis of 1-hydroxy-cyclohexyl-phenylketone. 6.6 g of 1-bromo-cyclohexyl-phenylketone obtained with Method G (24.7 mmoles), were dispersed in 6 g of NaOH 30% and heated to 80 C.; 100 mg of benzyl-triethylammonium chloride were added in two portions, and the mixture was stirred at 80 C. for one hour. The organic phase was separated and washed warm with 10 ml of water set a pH 3 with concentrated HCl. The organic phase crystallized from petroleum ether 40-65 C. obtaining 3 g of a whitish solid (59%), mp 45-46 C. H1NMR(300 MHz, CDCl3): 8: 7.97-8.07 (d,2H); 7.40-7.60 (m,3H); 3.45 (s, 1H); 1.97-2.12 (m,2H); 1.60-1.87 (m,7H); 1.25-1.45 (m,1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.2% | With tetrabutylammomium bromide; sodium hydroxide; In tetrachloromethane; at 80 - 90℃; for 12h; | n a 1000 ml three-necked flask, 178.7 g of crude cyclohexyl phenyl ketone, 5.36 g of tetrabutylammonium bromide, 220 g of carbon tetrachloride and 76 g of sodium hydroxide were added, and the condenser was connected.The mixture was heated and stirred at 80-90 C for 12 hours. After the reaction was completed, it was cooled to room temperature, diluted with 200 g of dichloromethane, and the organic layer was washed with saturated brine until neutral. The finished photoinitiator 184 was 174.8 g, and the yield was 90.2% |
86.62% | With di-tert-butyl peroxide; In dichloromethane; at 50℃;Sonication; | 94.14g (0.5mol) of cyclohexyl phenyl ketone, dichloromethane (200ml), 231.15g (5mol) of di-tert-butyl peroxide were uniformly mixed, placed in an ultrasonic rod (80KHz), stirred vigorously, and the reaction was controlled. The temperature is around 50 C,The reaction was carried out and the progress of the reaction was monitored using TLC or GC.After the completion of the reaction, a sodium hydrogen sulfite solution (containing 187.3 g of sodium hydrogen sulfite) was slowly added dropwise to the reaction system to carry out a quenching reaction.Stir until no peroxide is detected with the starch-potassium iodide test paper, then stir for 30 min. Then continue testing with the test paper until there is no peroxide.After standing and layering, the organic layer is washed with water to neutrality, and the dichloromethane is recovered by atmospheric pressure, and the solvent is further recovered by reducing the pressure.When the solvent and the low-boiling substance were removed, the distillation was carried out under reduced pressure, and a fraction of 107-109 C / 1.8 kPa was collected, and the mixture was cooled to a white solid.88.47 g was obtained, the yield was 86.62%, and the GC content was 99.58%. |
85% | With dihydrogen peroxide; In dichloromethane; at 30℃;Microwave irradiation; | 94.1 g (0.5 mol) of cyclohexyl phenyl ketone, 250 mL of dichloroethane, and 170.0 g (1.5 mol) of 30% hydrogen peroxide solution were uniformly mixed and placed in a microwave reactor (power: 800 W), stirred vigorously, and the reaction temperature was controlled. The reaction was performed at about 30C. The reaction was monitored by TLC or GC. After the reaction was completed, microwave radiation was added to the reaction system to slowly add sodium bisulfite water.The solution (containing 187.3g of sodium bisulfite) was subjected to extraction for 2h, allowed to stand, separated, and the organic phase was washed with water. The solvent was recovered after decompression at atmospheric pressure.Solvents and low-boiling impurities were removed and purified by vacuum distillation to collect 117-119C/0.3mmHg fractions.Colorless oil 1-hydroxycyclohexyl phenyl ketone 86.8g,Place a white solid with a GC content of 99.2% and a yield of 85.0%.It can then be crystallized using petroleum ether to give white crystals. |
81.2% | A 500 mL double-walled-jacket multi-necked flask, fitted with a mechanical stirrer, reflux condenser, thermometer and a dropping funnel connected to a thermostat, is charged with 75.3 g (400 mmol) cyclohexyl phenyl ketone, 2.58 g (8 mmol) tetrabutylammonium bromide and 373.3 g (2.80 mol) 30% aqueous sodium hydroxide solution. This is heated with stirring to 82-85 00 and within 90 minutes a solution of 96.6 g (408 mmol)hexachloroethane in 199 g tetrachloroethylene is added. The reaction mixture is stirred for another 3 hours at 84 00. The temperature is then lowered to 60 00 and left unstirred for phase separation. The lower organic phase is split off; the aqueous phase is extracted with 50 g tetrachloroethylene, the organic phases are combined and 100 g water added. pH is then adjusted to 6.0 using 5% acetic acid. The organic phase is splitoff and the product is vacuum distilled.Yield: 66.3 g (81.2%) (1 -hydroxycyclohexyl) phenyl ketone (Irgacure 184) as a pale yellow oil;b.p. 143 00 0.7 mbar, 95% purity (GO). NMR data are identical with the data of anauthentic reference sample.Tetrachloroethylene (b.p. 55 00 200 mbar) is nearly quantitatively recovered (97%, 99.5% purity). | |
46.5 g | With hydrogen bromide; In dimethyl sulfoxide; at 110℃; for 16h; | 47 g (0.25 mol) of cyclohexyl phenyl ketone was dissolved in 282 ml of dimethyl sulfoxide and stirred at room temperature.A mass fraction of 48% hydrobromide 4.2 g (0.025 mol) was added dropwise, and the temperature was raised to 110 C. The reflux reaction was carried out for 16 h.The reaction was confirmed by HPLC, and the content of 1-hydroxycyclohexyl phenyl ketone was 95.2%.The reaction was stopped, and dimethyl sulfoxide was recovered by distillation under reduced pressure to obtain 52.4 g of a brown gum.Distillation under reduced pressure gave 47.3 g of light brown solid, which was again recrystallized to give 46.5 g of a white solid, content of 99.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen;palladium diacetate; Bathocuproine; In water; at 100℃; for 48h; | A mixture of 0.112 g (0.5 mmol) of palladium acetate and 0.018 g (0.5 mmol) ofbathocuproine in 100 mL of water is stirred at room temperature for 24 hours. 1.88 g(10 mmol) of epoxide (product of example 13) are then added and the reaction mixture isstirred at 100C under an oxygen atmosphere for 48 hours. After cooling to roomtemperature, the product is extracted twice using 150 mL of ethyl acetate each time. Thecombined organic phases are dried over sodium sulphate and concentrated by evaporation,and the crude product is chromatographed on silica gel (hexane:ethyl acetate 9:1). Thedesired product is obtained in the form of a light-yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1817 g | With bromine; In dichloromethane; at 20℃;Large scale; | Step one: to a solution of 2063 grams of diol 5 in 20 L of CH2Cl2 at room temperature was slowly added 1598 grams of Br2 (1 eq), the reaction mixture was stirred while maintaining the reaction system at room temperature, and acidic HBr gas released was absorbed by water. The reaction progress was monitored by TLC until the completion was detected. Water of equal volume was thus added, and organic layer was separated. The solvent was then recovered and the concentrated crude product was subjected to distillation under reduced pressure to yield 1817 grams of hydroxyketone 2 as white solid. Product 2 has the following spectroscopic characterization data: 1H-NMR (CDC13, ppm): 8.01-8.00 (d, 2H), 7.55-7.43 (m, 3H), 3.41 (s, 1H), 2.07-2.04 (m, 2H), 1.82-1.66 (m, 8H); 13C-NMR (CDC13, ppm): 205.5, 135.2, 132.3, 129.5, 128.2, 78.7, 35.3, 25.3, 21.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol;Reflux; | General procedure: A solution of equimolar amounts of hydroxy ketone 1-4 and ethyl acetoacetate and 0.1 equiv of sodium ethoxide in anhydrous ethanol was heated under reflux. When the reaction was complete, a part of the solvent was distilled off, and the residue was neutralized with dilute (1 : 1) hydrochloric acid and extracted with methylene chloride.The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was distilled under reduced pressure to isolate 3-acetyl-4,5,5-trimethylfuran-2(5H)-one (5) [5], 3-acetyl-5,5-dimethyl-4-phenylfuran-2(5H)-one (6) [7], 3-acetyl-4-methyl-5,5-pentamethylenefuran-2(5H)-one (7) [6], or 3-acetyl-5,5-pentamethylen-4-phenylfuran-2(5H)-one (8) [6]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Irgacure 184 (0.51 g, 2.50 mmol) in 3 mL of dry DMF was addedto NaH (60% dispersion in mineral oil, 0.14 g, 5.8 mmol) dropwise at0 C under nitrogen. After stirring for 45 min at room temperature,TBBr (1.27 g, 5.8 mmol) in 2 mL of dry DMF was added dropwiseand the solution was stirred at room temperature for 24 h. Thereaction was quenched by addition of water and the resulting white precipitate was isolated, washed with hexane (310 mL)and dried under reduced pressure to give the crude product. Finalpurification by column chromatography on silica gel using hexaneinitially and gradually changing to CH2Cl2 as eluent, afforded thepure product as a viscous liquid in 40% yield.1H NMR (CDCl3, 400 MHz, d): 1.37 (s, 9H, CH3), 1.50-1.78 (m, 6H,CH2), 2.06 (d, 4H, ring-CH2), 3.88 (s, 2H, CH2O), 5.75 (s, 1H,CH2 = C), 6.12 (s, 1H, CH2 = C), 7.32 (t, 2H, Ar-H-m), 7.43 (t, 1H, Ar-H-p), 8.15 (d, 2H, Ar-H-o) ppm.13C NMR (CDCl3, 400 MHz, d): 21.44 (CH2), 25.49 (CH2), 28.01(CH3), 32.55 (CH2), 61.88 (CH2O), 80.97 (C(CH3)3), 84.05 (C-CH2),124.54 (CH2 = C), 128.19 (Ar-CH-m), 129.58 (Ar-CH-o), 132.61 (Ar-CH-p), 135.28 (Ar-C), 138.81 (CCH2), 164.91 (CO, ester), 203.80(CO, ketone) ppm.FTIR (ATR, cm1): 2927 (CH), 1694 (CO, ester), 1672 (CO,ketone), 1147 (CO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Next, 600 g of water was mixed with 188 g (0.7 mol) of (1-hydroxycyclohexyl) benzyl bromide. The mixture was stirred at 100 C. for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). After extracted with DCE and brine and evaporated to remove the solvent, (1-hydroxycyclohexyl)-phenyl-methanone was produced with a yield of 65%. (bp. 175 C./15 mmHg) |
Tags: 947-19-3 synthesis path| 947-19-3 SDS| 947-19-3 COA| 947-19-3 purity| 947-19-3 application| 947-19-3 NMR| 947-19-3 COA| 947-19-3 structure
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H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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