[ CAS No. 106797-53-9 ] {[proInfo.proName]}

Name: 106797-53-9|2-Hydroxy-1-(4-(2-hydroxyethoxy)phenyl)-2-methylpropan-1-one|98%
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Quality Control of [ 106797-53-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 106797-53-9 ]

SDS Specification

Alternatived Products of [ 106797-53-9 ]

Product Details of [ 106797-53-9 ]

CAS No. :	106797-53-9	MDL No. :	MFCD00085267
Formula :	C₁₂H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GJKGAPPUXSSCFI-UHFFFAOYSA-N
M.W :	224.25	Pubchem ID :	86266
Synonyms :

Calculated chemistry of [ 106797-53-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	59.91
TPSA :	66.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.28
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	1.01
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.7
Solubility :	4.47 mg/ml ; 0.0199 mol/l
Class :	Very soluble
Log S (Ali) :	-1.81
Solubility :	3.44 mg/ml ; 0.0153 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.58
Solubility :	0.594 mg/ml ; 0.00265 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 106797-53-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P273	UN#:	N/A
Hazard Statements:	H302-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 106797-53-9 ]

* 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 [ 106797-53-9 ]
Downstream synthetic route of [ 106797-53-9 ]

[ 106797-53-9 ] Synthesis Path-Upstream 1~3

1
[ 159119-01-4 ]
[ 106797-53-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 60℃; for 24 h; Schlenk technique	Taking a 25 ml Schlenk reaction tube, adding N - bromo succimide (NBS) 18 mg (0.1mmol) as catalyst, 4' - (2 - hydroxy ethoxy group) -2 - methylpropiophenone 105 mg (0.5mmol), dimethyl sulfoxide (DMSO) 1 ml as the oxidizing agent, carbonylating and solvent, for 100 °C stirring for 24 hours. After the reaction by adding ethyl acetate 15 ml, salt water 3 ml, ethyl acetate 3 times, the combined organic phase, column chromatography separation to obtain 2 - hydroxy -4 ' - (2 - hydroxy ethoxy group) -2 - methylpropiophenone pure product 103 mg, yield 92percent.
71%	With dihydrogen peroxide In dichloromethane at 30℃; Microwave irradiation	44.1 g (0.5 mol) of 4-(2-hydroxyethoxy)isobutyrophenone, 300 mL of dichloroethane and 283.3 g (2.5 mol) of 30percent hydrogen peroxide solution were uniformly mixed and placed in a microwave reactor (power of 500 W). , Stir vigorously, and control the reaction temperature at about 30 °C reaction, using TLC or GC to monitor the reaction, the reaction is complete, the microwave radiation, the reaction system was slowly added sodium bisulfite aqueous solution (containing 146g of sodium bisulfite), The reaction was extirpated for 2 h, allowed to stand, separated, and the organic phase was washed with water. The solvent was recovered by decompression at atmospheric pressure, and the residue was recrystallized from methanol.The white solid 2-hydroxy-1-(4-(2-hydroxyethoxy)phenyl)-2-methyl-1-propanone 79.6 g was obtained, HPLC content was 99.1percent, yield 71.0percent.

Reference： [1] Organic Letters, 2015, vol. 17, # 4, p. 876 - 879
[2] Patent: CN104710256, 2017, B, . Location in patent: Paragraph 0174-0177
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552[4] Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5
[5] Patent: CN107739303, 2018, A, . Location in patent: Paragraph 0017

2
[ 106797-52-8 ]
[ 106797-53-9 ]

Yield	Reaction Conditions	Operation in experiment
280 g	With sodium hydroxide In tetrachloromethane; N,N-dimethyl acetamide at 30℃; for 24 h;	In the clean 3LFour reaction bottles, add water 400 g,Stir intoSodium hydroxide400 g (10 mol),After the sodium hydroxide is completely dissolved,That is, the mass fraction of 50percent sodium hydroxide solution,Control reaction temperature 30 ,Slowly drop A: 408 g(1.63 mol) / carbon tetrachloride: 276 g (1.63 mol) / DMAC: 61 g,Control reaction temperature 30 reverseShould be 24h,The reaction ends with thickThe pH of the reaction solution was adjusted to neutral by hydrochloric acid, followed by the addition of 1.4 LofMethyl acetate,Stir for 10 minutes,Filter the by-product of sodium chloride in the feed,Filtrate static stratification,The lower aqueous phase is further added to 1LOf methyl acetate extraction once,After combining the organic phase,Atmospheric pressure recovery of methyl acetate to recover the application,When the amount of methyl acetate is relatively small,To vacuum concentration,Control temperature of 70 ,Vacuum 0.08Mpa,After concentrating for half an hour, the mass of the residue is twice as high as that of the residual solution1,2-dichloroethane,Stirring down to 0 crystallization,And the temperature is maintained for 2 h,Filtered crude product A wet weight 395 g, drying 315 g,The content is greater than 97percent and the molar yield is about 85percent.(3) crude C is refinedAdd 630 g of dichloroethane in a clean 1 L three-necked reaction flask, add the crude C315 g to the mixture, and then raise the temperature to 55 ° C,After the crude product was completely dissolved, 31.5 g of activated char was added, stirred for 1 hour with stirring, then filtered and washed with 50 g of dichloroethaneFilter cake, and finally combined filtrate and lotion into a clean 1L three mouth reaction flask, stirring down to 5 crystallization, filtration finishedDry weight 280 g, content greater than 99percent.

Reference： [1] Patent: US4922004, 1990, A,
[2] Patent: US4861916, 1989, A,
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552[4] Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5
[5] Patent: CN106365967, 2017, A, . Location in patent: Paragraph 0014; 0015; 0017; 0018; 0020; 0021; 0023-0027

3
[ 6192-44-5 ]
[ 106797-53-9 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 2, p. 548 - 552[2] Angew. Chem., 2014, vol. 53, # 2, p. 558 - 562,5

[ 106797-53-9 ] Synthesis Path-Downstream 1~78

1
[ 106797-53-9 ]
[ 5131-95-3 ]
[ 335287-94-0 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 14952 - 14958
[2]Journal of Physical Chemistry B,2001,vol. 105,p. 3405 - 3408
[3]Journal of the American Chemical Society,2002,vol. 124,p. 8532 - 8533

2
[ 375-95-1 ]
[ 106797-53-9 ]
2-hydroxy-4'-(2-perfluorononanoyloxyethoxy)-2-methylpropiophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 110℃; for 4h;	Into a 300 mL round-bottomed flask with a stirrer were charged 40 g of perfluorononanoic acid (compound i in the above-mentioned reaction equation; k=8) and 6.4 g of 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone (compound ii in the reaction equation), and the mixture was heated to 110 C. When the whole of the starting materials were turned into a melting state, the reaction system was started to be slowly stirred. The reaction was then continued for 4 hours. After the reaction, the reactant was once cooled to room temperature. It was then identified by gas chromatographic analysis that 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone was not present. Furthermore, the reactant was heated to 100 to 160 C. under reduced pressure so as to distill off remaining perfluorononanoic acid. The reactant was again cooled to room temperature to yield about 12 g of a white solid. The resultant white solid was analyzed by infrared spectroscopy, gel permeation chromatography, gas chromatography, gas chromatographic mass spectroscopy, and so on. As a result, it was identified that a target fluorine-containing photo initiator A, 2-hydroxy-4'-(2-perfluorononanoyloxyethoxy)-2-methylpropiophenone (compound iii in the reaction equation; k=8) was obtained as a main product. This white solid was used as the fluorine-containing photo initiator A in examples described hereinafter. Identification data on the photo initiator A: IR (FIG. 2): OH stretch at 3390-3500 cm-1; ester C=O stretch near 1770 cm-1; benzyl position C=O stretch near 1650 cm-1; benzene ring C=C stretch near 1600 cm-1; and perfluoroalkyl group C-F stretch near 1100-1200 cm-1.The white solid was dissolved into perf luorooctane, and the ultraviolet absorption spectrum thereof was measured. As a result, an absorption originating from ?-?* transition of the benzene ring of the target product was observed near a wavelength of 260 nm and an absorption originating from n-?* transition of the carbonyl of the benzoyl moiety of the target product was observed in the vicinity of a wavelength of 320 nm. A small amount of 2-(perfluorooctyl)ethyl acrylate was further added to this solution, and ultraviolet rays were radiated onto the solution. As a result, the absorption near 260 nm was largely reduced to suggest advance of the cleavage of the initiator and the addition thereof to the acrylate. Accordingly, from this viewpoint, it was also confirmed that the resultant white solid was made mainly of the target fluorine-containing photo initiator A, 2-hydroxy-4'-(2-perfluorononanoyloxyethoxy)-2-methylpropiophenone (compound iii in the reaction equation; k=8).

Reference： [1]Patent: US2004/181087,2004,A1 .Location in patent: Page 12-13

3
[ 106797-53-9 ]
[ 814-68-6 ]
[ 110430-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; quinoline; ice-water;	(c) 27.0 g (0.12 mol) of 4-(2-hydroxyethoxy)-phenyl 2-hydroxy-2-propyl ketone are dissolved in 240 ml of dioxane. 12.0 g (0.132 mol) of acryloyl chloride in 20 ml of dioxane are then added dropwise at room temperature with stirring, followed by 16.8 g (0.132 mol) of quinoline in 20 ml of dioxane. This is followed by stirring at 50 C. for 1 h, cooling down and discharge onto 1 l of ice-water. The mixture is extracted 3 times with 250 ml of ethyl acetate each time. Drying and concentrating of the organic phase gives 20.8 g of the photoinitiator in the form of a viscous oil. 1 H-NMR (CDCl3): delta 1.6 (s, 6 H, 2 CH3), 4.3 (m, 2 H, CH2), 4.6 (m, 2 H CH2), 5.3 (s, 1H, OH), 5.9-6.5 (m, 3 olefinic H), 7.0 (m, 2 aromatic H), 8.1 (m, 2 aromatic H) ppm. IR: nu 1710 (CO): 3500 (OH) cm-1.
	With triethylamine; In ethyl acetate; at 5 - 20℃; for 3.5h;	Material Preparation 3: 2959 Acrylate Ester; Irgacure 2959 Type I photoinitiator, 132 g, was added to ethyl acetate in a 2-liter, 3-neck round bottom flask equipped with overhead stirrer, thermocouple, condenser and addition funnel with a nitrogen inlet. Cold acryloyl chloride (Aldrich Chemical Company, Milwaukee, Wis.), 57.9 g, was added and the reactor was cooled to <5 C. with an ice bath. Triethylamine, 65 g, was added dropwise over 90 minutes, keeping reactor temperature below 10 C. The yellow ?slurry? was stirred for 2 hours at room temperature and a sample analyzed by FTIR. Very little hydroxyl functionality was observed and the reaction was judged to be complete. The product was suction filtered at room temperature and the filter cake rinsed with ethyl acetate twice. The product liquor was then poured into a 500 ml single neck flask and stripped on a rotary evaporator with light sparge of dry air at 40 C. for 2 hours. 163 g of viscous yellow liquid were recovered. Analyses by NMR and FTIR suggested near quantitative conversion (>97%) of the Irgacure 2959. For easier handling, the resin was diluted with hexanediol diacrylate (HDDA) to 75% w/w active 2959 acrylate ester.
	With triethylamine; In dichloromethane; at 0 - 20℃;	Preparation of Compound III; Synthesis of 3-(2-methylaziridin-l-yl)-propionic acid 2-[4-(2-hydroxy-2-methyl- propionyl)phenoxy] ethyl ester (AZHP); To a 200 mL flask were added triethylamine (5.57 g, 55.0 mmol), methylene chloride (50 mL) and 2-hydroxy-l-[4-(2-hydroxyethoxy)phenyl]-2-methyl-propan-l-one (Aldrich, 11.2 g, 50.0 mmol). The suspension was stirred and cooled to 0 0C. Acryloyl chloride (5.18 g, 55.0 mmol) was added dropwise to the reaction mixture over a period of 10 minutes and then the mixture was allowed to stir at ambient temperature overnight. Water (50 mL) was added to the reaction mixture, the organic layer was separated and washed 2X with water, dried over MgSO4, filtered and concentrated under vacuum to give an oil. Further purification was completed through column chromatography to give 5.42 g of colorless liquid (acrylic acid 2-[4-(2-hydroxy-2-methylpropionyl)phenoxy]ethyl ester).

	With triethylamine; In dichloromethane; at 0℃; for 1h;	2.5 g of compound (a1-1) (manufactured by Ciba Specialty Chemicals, tradename: IRGACURE 2959) and 2.3g of triethylamine were dissolved in 62 mL of dichloromethane to obtain a solution. While the solution was stirred at 0C,a solution having 1.0 g of acrylic acid chloride (compound (b1-1)) dissolved in 8 mL of dichloromethane was dropwiseadded to the solution. After completion of dropwise addition, the solution was stirred at 0C for 1 hour to obtain a solutioncontaining compound (c1-1).
		(a) 2-Hydroxy-2-methyl-p-hydroxyethylether phenylacetone (2959) (22.43 g, 0.10 mol),Triethylamine (10.81 g, 0.11 mol) and 150 mL of methylene chloride solution were added to a 500-ml three-necked flask equipped with a mechanical stirring and a constant pressure addition funnel, and stirred at room temperature for 10 min.Then, a solution of acryloyl chloride (9.96 g, 0.12 mol) in 100 mL of dichloromethane was added dropwise to the three-necked flask under ice-cooling, and the ice bath was removed after 2 h was added, and the reaction was continued for 6 h at room temperature.After the reaction, the product was filtered, the filtrate was washed twice with deionized water, 1 mol·L-1 hydrochloric acid and 1 mol·L-1 aqueous sodium bicarbonate solution, the organic layer was dried over anhydrous Na 2 SO 4 , filtered, and the solvent was distilled off under reduced pressure. The crude product was obtained, which was then recrystallized using ethanol as a solvent to finally obtain the intermediate product 2959Ac.

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 3403 - 3409
[2]Patent: US4922004,1990,A
[3]Patent: US7524565,2009,B2 .Location in patent: Page/Page column 8
[4]Patent: WO2010/65355,2010,A1 .Location in patent: Page/Page column 24
[5]Patent: EP2792665,2014,A1 .Location in patent: Paragraph 0249
[6]Patent: CN107868034,2018,A .Location in patent: Paragraph 0045; 0046; 0048

4
[ 106797-53-9 ]
[ 814-68-6 ]
[ 110538-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	EXAMPLE 3 4-(2-Acryloyloxyethoxy)-phenyl 2-acryloyloxy-2-propyl ketone 27.0 g (0.12 mol) of the 4-(2-hydroxyethoxy)-phenyl 2-hydroxy-2-propyl ketone obtained in Example 2a are esterified with 24.0 g (0.264 mol) of acryloyl chloride and 26.4 g (0.264 mol) of triethylamine. Corresponding working up gives 22.8 g of the photoinitiator with a melting point of 71 C.

Reference： [1]RSC Advances,2016,vol. 6,p. 31692 - 31697
[2]Patent: US4922004,1990,A

5
[ 106797-52-8 ]
[ 106797-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine; In ice-water; ethanol; acetic acid; ethyl acetate;	(b) 250 g (1.0 mol) of 4-(2-acetoxyethyloxy)-phenyl 2propyl ketone are dissolved in 200 ml of glacial acetic acid, and 192 g (1.2 mol) of bromine are added at 25 C. with stirring in the course of 2 hours. This is followed by about 10 hours of stirring and subsequent discharge in 3 l of glacial acetic acid. The product is extracted with ethyl acetate. The combined extracts are dried, and concentrating gives 365 g of a viscous oil. This oil is dissolved in 1 l of ethanol, and 380 g of 32% strength sodium hydroxide solution are then added at 25 C. with stirring in the course of 20 minutes. This is followed by 10 minutes of stirring and the subsequent removal of ethanol. The oily residue is discharged into 3 l of ice-water, and this mixture is extracted repeatedly with a total of 1.5 l of ethyl acetate. Drying, filtering and concentrating of the solution gives 250 g of isolated oily crude product. Recrystallization from acetone/petroleum ether and/or chromatographic purification gives 145 g of 4-(2-hydroxyethoxy)-phenyl 2-hydroxy-2-propyl ketone in the form of a colourless solid substance having a melting point of 88-90 C.
	With sodium hydroxide; bromine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; acetic acid; ethyl acetate;	(b) 250 g (1.0 mole) of 4-(2-acetoxyethoxy)-phenyl 2-propyl ketone are dissolved in 200 ml of glacial acetic acid, and 192 g (1.2 moles) of bromine are added, with stirring, at 25 C. and in the course of 2 hours. Stirring is continued for approx. 10 hours and the mixture is then poured into 3 l of glacial acetic acid. The product is extracted with ethyl acetate. The combined extracts are dried, and concentrating the latter gives 365 g of a viscous oil. This is dissolved in 1 l of ethanol, and 380 g of 32% strength sodium hydroxide solution are added, with stirring, at 25 C. and in the course of 20 minutes. Stirring is continued for 10 minutes, and the ethanol is then removed. The oily residue is poured into 3 l of ice water, and this mixture is extracted several times with a total of 1.5 l of ethyl acetate. 250 g of oily crude product are isolated after drying, filtering and concentrating the solution. Recrystallization from acetone/petroleum ether and/or purification by chromatography gives 145 g (65%) of 4-(2-hydroxyethoxy)-phenyl 2-hydroxy-2-propyl ketone in the form of a colourless solid of melting point 88-90 C.
280 g	With sodium hydroxide; In tetrachloromethane; N,N-dimethyl acetamide; at 30℃; for 24h;	In the clean 3LFour reaction bottles, add water 400 g,Stir intoSodium hydroxide400 g (10 mol),After the sodium hydroxide is completely dissolved,That is, the mass fraction of 50% sodium hydroxide solution,Control reaction temperature 30 ,Slowly drop A: 408 g(1.63 mol) / carbon tetrachloride: 276 g (1.63 mol) / DMAC: 61 g,Control reaction temperature 30 reverseShould be 24h,The reaction ends with thickThe pH of the reaction solution was adjusted to neutral by hydrochloric acid, followed by the addition of 1.4 LofMethyl acetate,Stir for 10 minutes,Filter the by-product of sodium chloride in the feed,Filtrate static stratification,The lower aqueous phase is further added to 1LOf methyl acetate extraction once,After combining the organic phase,Atmospheric pressure recovery of methyl acetate to recover the application,When the amount of methyl acetate is relatively small,To vacuum concentration,Control temperature of 70 ,Vacuum 0.08Mpa,After concentrating for half an hour, the mass of the residue is twice as high as that of the residual solution1,2-dichloroethane,Stirring down to 0 crystallization,And the temperature is maintained for 2 h,Filtered crude product A wet weight 395 g, drying 315 g,The content is greater than 97% and the molar yield is about 85%.(3) crude C is refinedAdd 630 g of dichloroethane in a clean 1 L three-necked reaction flask, add the crude C315 g to the mixture, and then raise the temperature to 55 C,After the crude product was completely dissolved, 31.5 g of activated char was added, stirred for 1 hour with stirring, then filtered and washed with 50 g of dichloroethaneFilter cake, and finally combined filtrate and lotion into a clean 1L three mouth reaction flask, stirring down to 5 crystallization, filtration finishedDry weight 280 g, content greater than 99%.

Reference： [1]Patent: US4922004,1990,A
[2]Patent: US4861916,1989,A
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 548 - 552
Angew. Chem.,2014,vol. 53,p. 558 - 562,5
[4]Patent: CN106365967,2017,A .Location in patent: Paragraph 0014; 0015; 0017; 0018; 0020; 0021; 0023-0027

6
[ 7743-98-8 ]
[ 106797-53-9 ]
C₂₀H₃₀O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of comparative initiator Comp-INI-3; The comparative initiator Comp-INI-3 was prepared according to the following synthesis scheme: [Show Image] To a solution of 2-[2-(2-methoxyethoxy)ethoxy] acetic acid (2.7 g, 0.015 mol) in N,N-dimethylacetamide (50 mL), 1,1-carbonyldiimidazole (3.3 g, 0.0165 mol) was added in portions. The reaction mixture was allowed to stir for 30 minutes at room temperature resulting in the formation of the imidazole intermediate. Irgacure 2959 (3.4 g, 0.015 mol) was added and the mixture was stirred for about 48 hours at room temperature. The reaction mixture was cooled to -10C, diluted with distilled water (100 mL) and extracted with methyl-tert-butylether (2x150 mL). The organic layer was separated and dried over MgSO4. After evaporation of the solvent, the product was purified on a Prochrom LC80 Column (Novasep, Inc) using n-hexane / ethyl acetate (50/50) as eluent, to afford 2.4 g of a clear oil.

Reference： [1]Patent: EP2033949,2009,A1 .Location in patent: Page/Page column 35

7
[ 106797-53-9 ]
[ 106-89-8 ]
[ 1145780-71-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium hydroxide; tetra(n-butyl)ammonium hydrogen sulfate; In 1,2-dimethoxyethane; water;	Example 1A 2-Hydroxy-2-methyl-1-[4-(2-oxiranylmethoxyethoxy)phenyl]propan-1-one Epichlorohydrin (24 g, 0.261 mol) is added to a mixture of 16.31 g (0.408 mol) of sodium hydroxide, 45 ml of water, and 0.761 g (2.24 mmol) of tetrabutylammonium hydrogen sulfate that is previously cooled in an ice-water bath for 20 minutes. To this mixture is added dropwise over 45 minutes with rapid stirring, a solution of 10.32 g (46.0 mmol) of 2-hydroxy-1-[4-(2-hydroxy-ethoxy)phenyl]-2-methylpropan-1-one in 95 ml of 1,2-dimethoxyethane. The reaction mixture is stirred overnight at room temperature. The aqueous layer is removed, and the organic layer is concentrated. Purification by flash chromatography on silica gel (1:1 heptane:ethyl acetate) affords 9.20 g (71% of theoretical yield) of the title compound, a pale yellow liquid.

Reference： [1]Patent: US2009/104464,2009,A1

8
[ 13048-33-4 ]
[ 106797-53-9 ]
[ 818-61-1 ]
C₂₅H₃₆N₂O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Material Preparation 4: 2959/HEA MDI Diacrylate; Methylene diphenyl diisocyanate (Mondur ML, Bayer), 528 g, and hexanediol diacrylate (HDDA), 605 g, were stirred in a 2-liter resin kettle equipped with overhead stirrer, thermocouple, condenser and air inlet. Dibutyltin dilaurate (DABCO T-12, Air Products), 0.81 g, and Irgacure 2959, 448.5 g, were added to the stirring mixture and the reactor was heated to 60 C. 2-HEA, 232.4 g, was then added slowly over 30 minutes, keeping peak temperature below 65 C. Subsequent reaction was monitored by FTIR. The constituents were heated for a total of 25 hours at which time, the reaction was deemed complete by both NMR and FTIR. An additional 605 g of HDDA were added, creating a 50% w/w concentration of 2959 urethane acrylate in monomer.

Reference： [1]Patent: US7524565,2009,B2 .Location in patent: Page/Page column 8

9
[ 1694-31-1 ]
[ 106797-53-9 ]
[ 869487-35-4 ]
[ 869487-36-5 ]
[ 75-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20 - 125℃; for 1h;Product distribution / selectivity;	Material Preparation 1: Irgacure 2959 Acetoacetate; Irgacure 2959 Type I photoinitiator Irgacure 2959 from Ciba-Geigy, 224.25 g, was added to 250 ml toluene in a 2-liter, 3-neck round bottom flask equipped with overhead stirrer, thermocouple, condenser and nitrogen inlet. 158.2 g tert-butyl acetoacetate from Eastman Chemical Company was added and the reactor was stirred at room temperature until homogeneous. The reactor contents were then heated to 110 C. and the reactor was held at that temperature for 30 minutes.After 1 hour of total heating time, the reactor was fitted with a distillation head and the toluene/t-butanol azeotrope was stripped off under moderate nitrogen flow until the pot temperature reached 125 C. At such time, the reactor contents were decanted into a 1-liter single neck round bottom flask and the yellow liquid was stripped on a rotary evaporator for 2 hours at 70 C. with a slight nitrogen sparge. 309 g of viscous yellow liquid were recovered. Analysis by NMR suggested near quantitative conversion of the Irgacure 2959 as a mixture of primary or tertiary esters. For easier handling, the resin was diluted with trimethylol propane (ethoxy) triacrylate (TMPEOTA) to 52% w/w active acetoacetate.

Reference： [1]Patent: US7524565,2009,B2 .Location in patent: Page/Page column 7

10
[ 106797-53-9 ]
[ 625-36-5 ]
[ 110430-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; In acetone; at -5℃; for 10.5h;Heating / reflux;Product distribution / selectivity;	Synthesis of 4-(2-acryloyloxyethoxy)phenyl-2-hydroxy-2-propyl ketone (INI-1) 5.6 g (25 mmol) <strong>[106797-53-9]2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone</strong> and 60 mg BHT were dissolved in 100 ml acetone. 19 g (0.1375 mol) K2CO3 was added and the reaction mixture was cooled to - 5C. 9.5 ml (12.7 g, 0.1 mol) 3-chloropropionyl chloride was added over 30 minutes. The reaction mixture was refluxed for 10 hours and the conversion of <strong>[106797-53-9]2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone</strong> to 4-(2-acryloyloxyethoxy)phenyl-2-hydroxy-2-propyl ketone was determined by GC as disclosed above. After 10 hours, the conversion proved to be 94.3%. Conventional isolation procedure can be used to isolate 4-(2-acryloyloxyethoxy)phenyl-2-hydroxy-2-propyl ketone.
	With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; In acetone; at -5℃; for 10.5h;Reflux;	5.6 g (25 mmol) <strong>[106797-53-9]2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone</strong> (STIN-1) and 60 mg BHT were dissolved in 100 mL acetone. 19 g (0.1375 mol) K2CO3 was added and the reaction mixture was cooled to -5C. 9.5 mL (12.7 g, 0.1 mol) 3-chloropropionyl chloride was added over 30 minutes. The reaction mixture was refluxed for 10 hours and the conversion of <strong>[106797-53-9]2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone</strong> to 4-(2-acryloyloxyethoxy)phenyl-2-hydroxy-2-propyl ketone was determined by GC as disclosed above. After 10 hours, the conversion proved to be 94.3%. Conventional isolation procedure can be used to isolate 4-(2-acryloyloxyethoxy)phenyl-2-hydroxy-2-propyl ketone.

Reference： [1]Patent: EP2065362,2009,A1 .Location in patent: Page/Page column 24-25
[2]Patent: EP2199273,2010,A1 .Location in patent: Page/Page column 36; 37

11
[ 106797-53-9 ]
[ 625-36-5 ]
[ 1159136-23-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; In acetone; at -10 - 20℃; for 24.6667h;	EXAMPLE 1; This example illustrates the superior selectivity and the ease of isolation procedure when using a suspended inorganic base instead of a nitrogen base. This is exemplified by the synthesis of 4-(2-acryloyloxyethoxy)phenyl-2-hydroxy-2-propyl ketone. [Show Image] Synthesis of the intermediate INT-1 INT-1 or 4-(2-(3-chloropropionyloxy)ethoxy)phenyl-2-hydroxy-2-propyl-ketone was prepared as follows: 40.4 g (0.18 mol) 4-(2-hydroxyethoxy)phenyl-2-hydroxy-2-propyl-ketone (Darocur 2959) was dissolved in 560 ml acetone and 29.1 ml (28.5 g, 0.36 mol) pyridine was added. The reaction mixture was cooled to -10C and 34.4 ml (45.7 g, 0.36 mol) 3-chloropropionyl chloride was added over 40 minutes, while the temperature was kept at -10C. The reaction was allowed to continue for 24 hours at room temperature. 400 ml water and 450 ml ethylacetate was added and the mixture was stirred until all precipitated salts were dissolved. The organic fraction was isolated, dried over MgSO4 and evaporated under reduced pressure. 400 ml hexane was added to the residue and the mixture was stirred for 2 hours. The crude 4-(2-(3-chloropropionyloxy)ethoxy)phenyl-2-hydroxy-2-propyl-ketone precipitated from the medium, was isolated by filtration, washed with hexane and dried. 48.3 g (96 %) of 4-(2-(3-chloropropionyloxy)ethoxy)phenyl-2-hydroxy-2-propyl-ketone was isolated. The product was used without further purification to study the elimination.

Reference： [1]Patent: EP2065362,2009,A1 .Location in patent: Page/Page column 15-16

12
[ 106797-53-9 ]
[ 15486-96-1 ]
[ 1159136-39-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	With pyridine; In acetone; at -10 - 20℃; for 5.5h;	Step 1: synthesis of INT-15 10.1 g (45 mmol) <strong>[106797-53-9]2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone</strong> was dissolved in 140 ml acetone. 7.1 g (90 mmol) pyridine was added and the reaction mixture was cooled to -10C. 16.2 g (90 mmol) 3-bromopropionyl chloride was added drop wise while the temperature was kept below 0C. The reaction was allowed to continue at 0C for 30 minutes, followed by 5 hours at room temperature. 200 ml water and 150 ml ethyl acetate were added to the reaction mixture. The organic fraction was isolated and the aqueous fraction was extracted with 200 ml ethyl acetate. The pooled organic fractions were dried over MgSO4 and evaporated under reduced pressure. 4-(2-(3-bromopropionyloxy)ethoxy)phenyl-2-hydroxy-2-propyl ketone was isolated by preparative column chromatography on a Prochrom LC80 column, using Kromasil 60A 10mu as silica and n.-hexane/ethyl acetate 72/28 as eluent at a flow rate of 150 ml/min. 5.4 g of 4-(2-(3-bromopropionyloxy)ethoxy)phenyl-2-hydroxy-2-propyl ketone (33 %) was isolated as a white crystalline product (TLC on Merck Kieselgel 254F60, eluent n.-hexane/ethyl acetate 40/60, Rf: 0.25)

Reference： [1]Patent: EP2065362,2009,A1 .Location in patent: Page/Page column 23-24

13
[ 106797-53-9 ]
[ 107-05-1 ]
[ 119462-60-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 14673 - 14675

14
[ 110430-09-6 ]
[ 106797-53-9 ]
[ 814-68-6 ]
[ 75-55-8 ]
[ 1228009-89-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water;	Synthesis of 3-(2-methylaziridin-1-yl)-propionic acid 2-[4-(2-hydroxy-2-methyl-propionyl)phenoxy]ethyl ester (AZHP) To a 200 mL flask were added triethylamine (5.57 g, 55.0 mmol), methylene chloride (50 mL) and 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-propan-1-one (Aldrich, 11.2 g, 50.0 mmol). The suspension was stirred and cooled to 0 C. Acryloyl chloride (5.18 g, 55.0 mmol) was added dropwise to the reaction mixture over a period of 10 minutes and then the mixture was allowed to stir at ambient temperature overnight. Water (50 mL) was added to the reaction mixture, the organic layer was separated and washed 2* with water, dried over MgSO4, filtered and concentrated under vacuum to give an oil. Further purification was completed through column chromatography to give 5.42 g of colorless liquid (acrylic acid 2-[4-(2-hydroxy-2-methylpropionyl)phenoxy]ethyl ester). To a 100 mL, one-neck, round bottom flask equipped with a magnetic stirrer were added starting material acrylic acid 2-[4-(2-hydroxy-2-methylpropionyl)phenoxy]ethyl ester (1.12 g, 4.00 mmol), 2-methylaziridine (0.60 g, 8.8 mmol) and methylene chloride (5 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then concentrated under reduced pressure for 30 minutes to obtain 1.31 g of Compound III as a viscous oil.

Reference： [1]Patent: US2010/137469,2010,A1

15
[ 108-30-5 ]
[ 106797-53-9 ]
[ 847934-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In toluene; for 5h;Inert atmosphere; Reflux;	A mixture of 500 mg (2.22 mmol) 1, 245 mg (2.45 mmol) succinic anhydride, 247 mg (2.47 mmol) TEA and 10 ml toluene is refluxed for 5 hours under nitrogen atmosphere. The reaction mixture is cooled to ambient temperature, solvent is evaporated under reduced pressure, and the residue is dissolved in 10 ml of ethyl acetate and washed with 5 ml of 1N HCl. Organic layer is dried over Na2SO4. The solvent is removed under reduced pressure and the obtained intermediate 2, is dried under vacuum at 30 C. The results of 1H-NMR (400 MHz, DMSO-D6) delta are: 1.35 (s, 6H), 2.47-2.54 (m, 4H), 4.27-4.26 (d, J=4 Hz, 2H), 4.370-4.358 (d, J=4.8 Hz, 2H), 5.68 (bs, 1H, OH), 7.03-7.01(d, J=8.8 Hz, 2H), 8.22-8.19(d, J=8.8 Hz, 2H), 12.24(bs, 1H, COOH). The mass is determined to be 325 (M+H) by mass spectroscopy. Two peaks are observed at 212 nm and 266 nm in UV-visible absorption spectra.
	With triethylamine; In acetonitrile; at 20℃; for 24h;	To a suspension of STIN-1 (44.9 g, 0.2 mol) in acetonitrile (500 mL), triethylamine (44.5 g, 0.44 mol) was added, to result in a clear solution. Succinic anhydride (22.0 g, 0.22 mol) was added and the reaction mixture was allowed to stir at room temperature for 24 hours. After evaporation of the solvent, the residual oil was dissolved in a mixture of distilled water (500 mL) and an aqueous solution of sodium hydroxide (1N) (110 mL) and extracted with ethyl acetate (500 mL). The organic layer was separated and the aqueous layer was acidified to pH = 1 with an aqueous solution of hydrochloric acid and extracted twice with dichloromethane (500 mL). The organic layer was separated, dried over MgSO4, filtered and evaporated. The residue was treated with n-hexane and cooled to 3C for 15 hours. The crude succinic acid mono-{2-[4-(2-hydroxy-2-methyl-propionyl)-phenoxy]-ethyl}ester was isolated by filtration. The product was purified on a Prochrom LC80 Column using dichloromethane / ethyl acetate (75/25) as eluent and Kromasil Si60 10 mm as silica, to afford 20.6 g of a pale yellow solid.

Reference： [1]Patent: US2010/168359,2010,A1 .Location in patent: Page/Page column 12
[2]Patent: EP2199273,2010,A1 .Location in patent: Page/Page column 55; 56

16
[ 1233349-74-0 ]
[ 106797-53-9 ]
[ 1233349-77-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide;dmap; In dichloromethane; at 0℃; for 3h;Inert atmosphere;	A solution of 0.589 g (2.8 mmol) of DCC in 3 ml of dichloro methane is added to a stirred mixture of 0.5 g (1A4 mmol) of 3, 0.256 g (1.14 mmol) of 4, catalytic amount of D-MAP, and 5 ml of dichloro methane at 0 C. under nitrogen atmosphere. Reaction mixture is stirred at 0 C. for 3 h, 5 ml of water is added and the mixture is extracted with dichloro methane, the organic layer is washed with 5 ml of IN HCl followed by brine. Organic layer is next dried over Na2SO4, the solvent is evaporated under reduced pressure, and the resultant crude (5), UVA 2, is purified by column chromatography on silica (100-200 mesh) in 50% n-hexane in ethyl acetate. 1H-NMR (400 MHz, CDCl3) delta: 1.54 (s, 6H), 1.63(S, 6H), 1.92(s, 314), 3.04-3.08(t, J=6.8 Hz, 2H), 4.20-4.23(m, 3H), 4.37-4.4 (t, J=6.8 Hz, 2H), 4.50-4.52 (t, J=4.8 Hz, 2H), 5.54-5.55 (t, J=1.6 Hz, 1H), 6.09 (s, 1H), 6.87-6.91(m, 2H), 7.16-7.21 (m, 2H), 7.39-7.44 (m, 2H), 7.87-7.91(m, 2H), 7.99(s, 1H), 8.04-8.08 (m, 2H). MS: M+H (644), M+Na (666). Three peaks are observed at 218 nm, 266 nm and 302 nm in UV Visible absorption spectra.

Reference： [1]Patent: US2010/168359,2010,A1 .Location in patent: Page/Page column 13; 14

17
2-(2’-vinyloxyethoxy)ethyl acrylate [ No CAS ]
[ 106797-53-9 ]
[ 1231708-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-tert-butyl-4-methyl-phenol;poly(vinylpyridine) chlorohydrate, cross-linked with 2percent divinyl benzene; at 55℃; for 16h;	7.5 g (33 mmol) STIN-1 was dissolved in 30 mL 2-(2-vinyloxyethoxy)ethyl acrylate. 70 mg BHT was added. The reaction mixture was heated to 55C. 0.94 g cross-linked poly(vinylpyridine) tosylate, cross-linked with 2% divinyl benzene (supplied by Aldrich), was added and the reaction was allowed to continue for 16 hours. A TLC analysis indicated a full conversion of both the primary and tertiary alcohol (Partisil KC18F, supplied by Whatman, eluent : MeOH/NaCl 0.5 M; Rf = 0.37). The catalyst was removed by filtration and the solution of INI-4 in 2-(2-vinyloxyethoxy)ethyl acrylate can directly be used to formulate radiation curable compositions.

Reference： [1]Patent: EP2199273,2010,A1 .Location in patent: Page/Page column 53

18
[ 106797-53-9 ]
[ 920-46-7 ]
[ 115055-21-5 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7790 - 7792

19
[ 68-11-1 ]
[ 106797-53-9 ]
[ 1254067-29-2 ]

Reference： [1]Materials Research Bulletin,2011,vol. 46,p. 244 - 251
[2]Chinese Journal of Chemistry,2011,vol. 29,p. 1961 - 1968

20
[ 1694-31-1 ]
[ 106797-53-9 ]
[ 869487-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 110 - 125℃;Inert atmosphere;	In a 2 L four-neck flask provided with a stirrer, a condenser, a thermocouple, and a nitrogen inlet tube, 250 mL of toluene and 224.25 g of IRGACURE 2959 of Ciba Specialty Chemicals Inc. were added and stirred at room temperature. Then, 158.2 g of tert-butyl acetoacetate was added to the resultant mixture, followed by stirring at 110C for 1 hour. Next, a distillation tube was attached to a reactor, and a toluene/tert-butanol azeotropic mixture was distilled off under a nitrogen stream until the inner temperature was 125C. When the inner temperature reached 125C, reaction was terminated, and the solvent was distilled off from the resultant reaction mixture to produce 309 g of a photoinitiator (69) described in the related art. Next, in a 200 mL three-neck flask provided with a stirrer, a condenser, and a thermocouple, 64 g of ethylene oxide-modified pentaerythritol tetraacrylate (Miramer 4004), 16 g of the compound (69), and 0.67 g of tetrabutylammonium bromide were added and stirred at room temperature for 24 hours to produce 80 g of Michael addition reaction product (A). During reaction preparation, a ratio between groups functioning as a Michael donor and groups functioning as a Michael acceptor was 1:9.3.

Reference： [1]Patent: EP2450344,2012,A1 .Location in patent: Page/Page column 22-23

21
[ 159119-01-4 ]
[ 106797-53-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-Bromosuccinimide; dimethyl sulfoxide; at 60℃; for 24h;Schlenk technique;	Taking a 25 ml Schlenk reaction tube, adding N - bromo succimide (NBS) 18 mg (0.1mmol) as catalyst, 4' - (2 - hydroxy ethoxy group) -2 - methylpropiophenone 105 mg (0.5mmol), dimethyl sulfoxide (DMSO) 1 ml as the oxidizing agent, carbonylating and solvent, for 100 C stirring for 24 hours. After the reaction by adding ethyl acetate 15 ml, salt water 3 ml, ethyl acetate 3 times, the combined organic phase, column chromatography separation to obtain 2 - hydroxy -4 ' - (2 - hydroxy ethoxy group) -2 - methylpropiophenone pure product 103 mg, yield 92%.
71%	With dihydrogen peroxide; In dichloromethane; at 30℃;Microwave irradiation;	44.1 g (0.5 mol) of 4-(2-hydroxyethoxy)isobutyrophenone, 300 mL of dichloroethane and 283.3 g (2.5 mol) of 30% hydrogen peroxide solution were uniformly mixed and placed in a microwave reactor (power of 500 W). , Stir vigorously, and control the reaction temperature at about 30 C reaction, using TLC or GC to monitor the reaction, the reaction is complete, the microwave radiation, the reaction system was slowly added sodium bisulfite aqueous solution (containing 146g of sodium bisulfite), The reaction was extirpated for 2 h, allowed to stand, separated, and the organic phase was washed with water. The solvent was recovered by decompression at atmospheric pressure, and the residue was recrystallized from methanol.The white solid 2-hydroxy-1-(4-(2-hydroxyethoxy)phenyl)-2-methyl-1-propanone 79.6 g was obtained, HPLC content was 99.1%, yield 71.0%.

Reference： [1]Organic Letters,2015,vol. 17,p. 876 - 879
[2]Patent: CN104710256,2017,B .Location in patent: Paragraph 0174-0177
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 548 - 552
Angew. Chem.,2014,vol. 53,p. 558 - 562,5
[4]Patent: CN107739303,2018,A .Location in patent: Paragraph 0017

22
[ 6192-44-5 ]
[ 106797-53-9 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 548 - 552
Angew. Chem.,2014,vol. 53,p. 558 - 562,5

23
[ 25726-04-9 ]
[ 106797-53-9 ]
[ 1599461-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap; In dichloromethane; at 5 - 20℃; for 1h;	2-Hydroxy-1 -[4-(2-hydroxyethoxy)phenyl]-2-methyl-propan-1 -one (Irgacure 2959, BASF) (3.36 g, 15 mmol) and 4-dimethylaminopyridine (0.1 g) are dissolved in 30 ml of dry pyridine. To this solution is added at 5-10C the solution of 2-oxo-2-phenyl-acetyl chloride (2.48 g,15 mmol) in 30ml dichloromethane and the resulting mixture is stirred for 1 h at room temperature. It is then diluted with 300 ml of water, and the organic layer is separated. The aqueous phase is extracted with 50 ml of dichloromethane. The combined organic phases are washed with 3 x 50 ml 2M-HCI and 30 ml 1 M-NaHC03, then dried over MgSC and evaporated. The residue is chromatographed on 130 g silica gel with hexane-ethyl acetate to afford 4.08g of the title compound as thick oil solidifying on standing. Recrystallization from hexane-dichloromethane affords the analytically pure sample as white crystals, mp. 52-54 C. H-NMR (CDCIs, 400 MHz, delta ppm): 8.08 (d, 2H), 8.04 (d, 2H), 7.68 (t, 1 H), 7.54-7.50 (m, 2H), 6.98 (d, 2H), 4.81 -4.79 (m, 2H, CH2), 4.42-4.40 (m, 2H, CH2), 4.20 (s, 1 H, OH), 1.63 (s, 6H, 2xCH3). 13C-NMR (CDCIs, 100.62 MHz, delta ppm): 202.59, 185.80, 163.51 , 161 .92, 135.12, 132.46, 132.26, 130.05, 128.96, 126.68, 1 14.17, 76.00, 65.56, 63.76, 28.63.

Reference： [1]Patent: WO2014/60450,2014,A1 .Location in patent: Page/Page column 41

24
[ 106797-53-9 ]
[ 1145780-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With bromotriphenylphosphonium bromide; triethylamine; In dichloromethane; for 2h;Cooling with ice; Inert atmosphere;	33.64 g TPP (0.15 mol) is weighed to a 1L flask and dissolved in 120 mL dry DCM . >8 mL Br2 is added slowly until a yellow colour persists. A white solid precipitates (Ph3PBr2) . A little TPP is added to get back to colourless. Solution is cooled (ice) and kept under N2. 2.5 mL TEA is added. 2-Hydroxy- 1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan- l-one (33.64 g, 150 mmol) is dissolved in 450 mL DCM + 25 mL TEA. This is then added to the cooled suspension over a period of ~ lh from an addition funnel, the ice is removed and the setup is left to heat to RT for 2h. 5 mL AcOH is added, reaction quenched with water and mix extracted with 3x100 mL brine + ( 100 mL brine + NaHCO3) . Organic phase dried (Na2S04), evaporated to dryness. Dried with oil pump/cold trap (~ 1 mBar) . To get rid of most of the TPPO : Redissolved in 250 mL ether. This causes precipitation of crystals (TPPO) . Cooled (freezer), filter through a cotton plug, rinse with cold ether, evaporate to dryness. 1H NMR (400 MHz, CDCl3 ) ; 8.07 (d, J = 8.8 Hz, 2H), 6.97 (d, J = 8.8 Hz, 2H), 4.36 (t, J = 6.2 Hz, 2H), 4.23 (s, 1H), 3.67 (t, J = 6.2 Hz, 2H), 1.63 (s, 6H) .

Reference： [1]RSC Advances,2014,vol. 4,p. 21410 - 21418
[2]Patent: WO2018/177488,2018,A1 .Location in patent: Page/Page column 12

25
[ 1613725-69-1 ]
[ 106797-53-9 ]
bis(2,4,6-trimethyl-benzoyl)-phosphinic acid 2-[4-{2'-hydroxy-2'-methyl-propanoyl}phenyloxy]-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In dichloromethane; at 20℃; for 12h;	The crude bis(2,4,6-trimethyl-benzoyl)-phosphinic acid chloride (5.45 mmol, 1 eq.), prepared according to example 1 1 , is dissolved in dichloromethane (20 ml) and the solution is subsequently added dropwise at room temperature to a solution of Irgacure 2959 (= 4[(2-hydroxyethoxy)-benzoyl]-1 -hydroxy-1 -methyl ethan) (1 .595 g, 7.12 mmol, 1 eq.) in dichloromethane (40 ml). The reaction mixture is stirred at room temperature for 12 h. The solvent is removed under reduced pressure. After recrystalli- zation from a toluene/hexane mixture (10 ml/5 ml, -15C), bis(2,4,6-trimethyl-benzoyl)- phosphinic acid 2-[4-{2'-hydroxy-2'-methyl-propanoyl}phenyloxy]-ethyl ester is obtained as a pale yellow (3.66 g, 91 %). 3 P-NMR (C6D6): delta = 0.710 ppm.

Reference： [1]Patent: WO2014/95724,2014,A1 .Location in patent: Page/Page column 79

26
[ 106797-53-9 ]
[ 98-59-9 ]
[ 119462-65-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; N,N-dimethyl acetamide; water; at 20 - 28℃; for 7h;	112.2 g (0.5 mol) IrgacureTM 2959 was suspended in 1 liter methylene chloride. 6.1 g (0.018 mol) tetrabutylammonium hydrogen sulfate was added and the mixture was stirred at room temperature. A solution of 62.4 g (1.56 mol) sodium hydroxide in 150 ml water was added while stirring. A solution of 103.9 g (0.545 mol) tosyl chloride in 300 ml methylene chloride and 5 ml dimethyl acetamide was added over 5 hours while keeping the temperature between 24 and 28 C. The reaction was allowed to continue for 2 hours at 20 C. The methylene chloride fraction was isolated and extracted twice with 500 ml watet The water fractions were extracted with 200 ml methylene chloride. The pooled methylene chloride fractions were dried over Mg504 and the solvent was removed under reduced pressure. The solid residue was treated with a mixture of 300 ml tert.butyl methyl ether and 200 ml hexane. The tosylate was isolated by filtration and treated for a second time with a mixture of 100 ml tert.butyl methyl ether and 200 ml hexane. The tosylate was isolated by filtration and dried. 173.8 g of the tosylate was isolated (yield: 92%, melting point 75 C.).
	With potassium hydroxide; In dichloromethane; at 25℃; for 2h;	HHMP (26.9 g, 0.12 mol), TsCl (19.0 g, 0.10 mol) and KOH (22.4 g, 0.40 mol) were dissolved in 300 mL of CH2Cl2 in a 500 mL three-necked round bottom flask, which was equipped with a mechanical stirrer and a condenser. The solution was stirred at ambient temperature (25 C) for 2 h and then washed three times with deionized water. The organic layer was dried over Na2SO4, and filtered, then distilled under vacuum. The crude product was purified by silica gel (200-300 mesh) column chromatography using ethyl acetate and methylene chloride (1:20v/v) as an elution and the yield was 62.5%. The synthesis process is shown in Scheme 1. (0006) FTIR (KBr, cm-1): 3456 cm-1 (-OH), 3062 cm-1 (=C-H), 2984 cm-1, 2865 cm-1 (-CH3, -CH2), 1663 cm-1 (>C=O), 1598 cm-1, 1445 cm-1 (-C6H5), 1359 cm-1 (-SO2-), 1250 cm-1 1020 cm-1 (Ar-O-C). (0007) 1H NMR (400 MHz, CDCl3, ppm): 8.03, 7.82, 7.35, 6.84 (Ar-H), 4.42-4.40 (CH2CH2), 2.45 (ArCH3), 1.62 (CH3CCH3).
	With potassium hydroxide; In dichloromethane; at 20℃; for 2h;	(1) Photoinitiator 2959 (26.9 g, 0.12 mol), p-toluenesulfonyl chloride (TsCl) (19.0 g, 0.10 mol), KOH (22.4 g, 0.40 mol) was dissolved in 300 mL of dichloromethane and stirred at room temperature for 2 h. ;(2) The solution obtained in the step (1) is washed with deionized water for 3 times, and the organic phase is combined. The organic phase is dried over anhydrous sodium sulfate, and the supernatant is collected by suction filtration, and the supernatant is evaporated to dryness by a rotary evaporator. The solvent obtained the photoinitiator 2959-Tos crude product, and the crude product was purified by column chromatography. The eluent was a mixture of ethyl acetate and dichloromethane (volume ratio 1:4).

Reference： [1]Patent: US2019/144696,2019,A1 .Location in patent: Paragraph 0247-0248
[2]Polymer,2014,vol. 55,p. 3656 - 3665
[3]Patent: CN110156615,2019,A .Location in patent: Paragraph 0090-0092

27
[ 106797-53-9 ]
[ 335287-94-0 ]

Reference： [1]Journal of Physical Chemistry A,2014,vol. 118,p. 8701 - 8707

28
[ 335-64-8 ]
[ 106797-53-9 ]
perfluorooctanoic acid 2-[4-(2-hydroxy-2-methylpropionyl)phenoxy]ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With triethylamine; In dichloromethane; for 5h;Cooling with ice;	A mixture of 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone (2.24 g, 0.01 mol), triethylamine (1.01 g, 0.01 mol), and methylene dichloride (80 mL) were added into a 250 mL round-bottom flask equipped with stirrer, dropping funnels and stirred in ice bath. The mixture of PFOC (4.325 g, 0.01 mol) and dichloromethane (40 mL) was added dropwise over 2 h. Then the ice bath was removed and the mixture was stirred for another 3 h. The process of the reaction was monitored by TLC. The reaction mixture was washed by water and dried overnight by anhydrous sodium sulfate. The solvent was evaporated under vacuum and a yellow solid was obtained. The crude product was purified by column chromatography with ethyl acetate and methylene dichloride (1:2 v/v) as eluent to obtain a yellow solid. Yield: 2.82 g (43%).

Reference： [1]Polymer,2015,vol. 71,p. 93 - 101

29
[ 79-41-4 ]
[ 106797-53-9 ]
[ 115055-21-5 ]

Yield	Reaction Conditions	Operation in experiment
86.8%	With methanesulfonic acid; In toluene; at 100℃; for 4h;Inert atmosphere;	250mL four-necked flask was weighed in a dry, it was fitted with a thermometer, water separator, condenser, into nitrogen, were added to the flask 0.02mol (about 1.72g) of methacrylic acid, 0.01g paraben ether and 50mL of toluene, mixed evenly added 0.02mol (about 4.48g) 2959, stirring to completely dissolve the catalyst was added 0.04g of methane sulfonic acid, adjusting the reaction temperature to 100 , the reaction 4h.After completion of the reaction, toluene was removed by rotary evaporator to give the crude product, the crude product was dissolved in methylene chloride, and washed with deionized water repeatedly and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate after washing the organic phase was dried, filtered off magnesium sulfate, the organic phase was collected and further purified by column chromatography, where the silica gel column with a developing solvent was a mixed solvent of petroleum ether and ethyl acetate in a ratio of V (petroleum ether): V (ethyl acetate) = 10 : 1, to give a final 86.8% 5.13g pale yellow liquid 2959-MMA, yield.

Reference： [1]Patent: CN105859551,2016,A .Location in patent: Paragraph 0019; 0020

30
[ 53913-96-5 ]
[ 106797-53-9 ]
C₂₀H₂₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		To an ice-cold solution of Irgacure 2959 (1.12 g, 4.99 mmol) andTEA (1.92 g, 18.97 mmol) in 2.5 mL of dry THF under nitrogen, TBBr(1.10 g, 4.98 mmol) in 2.5 mL dry THF was added dropwise. Thesolution was stirred at 60 C for 24 h under nitrogen. Afterevaporation of the solvent, the residue was diluted with 15 mLof CH2Cl2 and then extracted with distilled water (34 mL). Theorganic layer was dried over anhydrous sodium sulfate,filtered andevaporated under reduced pressure. The residue was purified byrecrystallization from methanol to give the pure product as a whitesolid (mp = 46 C) in 76% yield.1H NMR (CDCl3, 400 MHz, d): 1.42 (s, 9H, CH3), 1.56 (s, 6H, CH3),3.81 (t, 2H, CH2O), 4.15 (t, 2H, CH2O), 4.19 (s, 2H, CH2O), 5.75(s, 1H, CH2 = C), 6.14 (s, 1H, CH2 = C), 6.90 (d, 2H, Ar-H), 7.98 (d, 2H,Ar-H) ppm.13C NMR (CDCl3, 400 MHz, d): 28.04 (CH3), 28.68 (C(CH3)3),67.57, 68.98, 69.65 (CH2O), 75.74 (COH), 80.99 (C(CH3)3),115.00 (Ar-CH), 124.84 (CH2 = C), 125.98 (Ar-C), 132.32 (Ar-CH),138.41 (CCH2), 162.65 (Ar-CO), 165.03 (CO, ester), 202.56(CO, ketone) ppm.FTIR (ATR, cm1): 3420 (OH), 2970 (CH), 1720 (CO, ester),1663 (CO, ketone), 1133 (CO).

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 329,p. 77 - 87

31
[ 30674-80-7 ]
[ 106797-53-9 ]
C₁₉H₂₅NO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dibutyltin dilaurate; In dichloromethane; at 20℃; for 3h;Inert atmosphere;	To a solution of the Irgacure 2959 (3.09 g, 13.80 mmol) inanhydrous CH2Cl2 (6 mL), a 1% solution of dibutyltin dilaurate inanhydrous CH2Cl2 (4 mL) followed by IEM (13.80 mmol) wereadded dropwise under nitrogen. The solution was stirred for 3 h atroom temperature and concentrated under reduced pressure toleave the crude product. The crude product was purified by columnchromatography on silica gel using hexane initially and graduallychanging to ethyl acetate as eluent. The pure product was obtainedas a white solid (mp = 81-82 C) in 50% yield.1H NMR (CDCl3, 400 MHz, d): 1.56 (s, 6H, CH3), 1.86 (s, 3H, CH3),3.45 (t, 2H, CH2N), 4.17 (t, 4H, CH2O), 4.39 (t, 2H, CH2O), 5.52(s, 1H, CH2 = C), 6.04 (s, 1H, CH2 = C), 6.89 (d, 2H, Ar-H), 7.99 (d, 2H,Ar-H) ppm. 13C NMR (CDCl3, 400 MHz, d): 18.28 (CH3), 28.67 (CH3COH),40.28 (CH2N), 63.04, 63.60, 66.53 (CH2O), 75.82(CH3COH), 113.33 (Ar-CH), 126.09 (CH2 = C), 126.28 (Ar-C),132.39 (Ar-CH), 135.89 (CCH2), 156.02 (CO, urethane), 162.30(ArCO), 167.24 (CO, ester), 202.58 (CO, ketone) ppm.FTIR (ATR, cm1): 3433 (NH), 3364 (OH), 2958 (CH), 1723(CO, ester), 1699 (CO, urethane), 1666 (CO, ketone), 1155(CO).MS (m/z): Calcd for C19H25NO7, 379.16. Found: 379.90 [M+H]+.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 329,p. 77 - 87

32
[ 106797-53-9 ]
C₁₂H₁₇O₇P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Take commercial photoinitiator 2-hydroxy-4 '- (2-hydroxyethoxy) -2-methyl-propiophenone (Darocur2959) 22.5g (0.1mol) in a three-necked flask, dissolved in toluene 40ml was added and stirred at state was added 7.1g (0.05mol) P2O5Powder, to be P2O5 After the powder was dispersed, stirred and heated to 65C , reacted for 2 hours, the system turbidity disappears, then added 0.9g (0.05mol) of deionized water, the reaction was continued for 1 hour lighter yellow transparent, stable acid value, was distilled off under reduced pressure toluene solvent, acid value was measured 360.2mgKOH / g.

Reference： [1]Patent: CN103333202,2016,B .Location in patent: Paragraph 0060; 0061

33
[ 106797-53-9 ]
[ 79-10-7 ]
[ 110430-09-6 ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 6014 - 6018

34
[ 24801-88-5 ]
[ 106797-53-9 ]
1-{4-[2-(3-triethoxysilanylpropylcarbamoyloxy)ethoxy]-phenyl}-2-hydroxy-2-methylpropane-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In toluene; at 70℃; for 24h;	To a suspension of 1 (10.0g, 44.6mmol) in toluene (100mL) stirred at 70C triethylamine (622muL, 4.46mmol) and 3-(triethoxysilyl)propyl isocyanate (13.25mL, 53.5mmol) were added and the resulting suspension was stirred at this temperature for 24h. After stirring for 2h, a clear solution was obtained. The solution was concentrated under reduced pressure and the residual oil was purified by column chromatography on silica gel using CH2Cl2-AcOEt (gradient 0-50% AcOEt) as eluent. The purified product was a pale yellow oil, which solidified quickly to form a white residue (18.0g, 38.2mmol, 86%). (0044) 1H NMR (400MHz, CDCl3): delta=0.62 (t, J=8Hz, 2H), 1.21 (t, J=8Hz, 9H), 1.58-1.62 (m, 8H), 3.16-3.21 (m, 2H), 3.78-3.83 (q, J=8Hz, 6H), 4.18-4.25 (m, 2H), 4.38-4.36 (m, 2H), 5.05 (bs, 1H-NH), 6.95 (d, J=8Hz, 2H), 8.05 (d, J=8Hz, 2H), ppm. (0045) 13C NMR (100MHz, CDCl3): delta=7.6, 18.3, 23.2, 28.7, 43.4, 58.4, 62.6, 66.7, 75.8, 114.1, 126.1, 132.4, 156.1, 162.4, 202.6, ppm. (0046) LRMS (ESI): [M+Na]+ 494.1.

Reference： [1]Polymer,2017,vol. 129,p. 207 - 220

35
C₂₂H₂₄ClO₄P [ No CAS ]
[ 106797-53-9 ]
C₃₄H₃₉O₈P [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 14306 - 14309
Angew. Chem.,2017,vol. 129,p. 14496 - 14499,4

36
[ 106797-53-9 ]
1-(4-(2-hydroxyethoxy)phenyl)-2-methoxy-2-methylpropan-1-one [ No CAS ]

Reference： [1]Patent: KR2017/125923,2017,A

37
[ 106797-53-9 ]
1-(4-(2-(2,4-dinitrophenoxy)ethoxy)phenyl)-2-methoxy-2-methylpropan-1-one [ No CAS ]

Reference： [1]Patent: KR2017/125923,2017,A

38
[ 106797-53-9 ]
1-(4-(2-(2,4-diaminophenoxy)ethoxy)phenyl)-2-methoxy-2-methylpropan-1-one [ No CAS ]

Reference： [1]Patent: KR2017/125923,2017,A

39
[ 110-87-2 ]
[ 106797-53-9 ]
2-hydroxy-2-methyl-1-(4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.7 g	With toluene-4-sulfonic acid; In tetrahydrofuran; at 20℃; for 3h;	IRGACURE2959 (2-hydroxy-1- (4- (2-hydroxyethoxy) phenyl) -2-methylpropan-1-one, 50.0 g, 223 mmol) was dissolved in THF (200 g) and p-Toluenesulfonic acid monohydrate (0.424 g, 2.23 mmol) was added, then 3,4-Dihydro-2H-pyran (23.4 g, 279 mmol) was added dropwise over 10 minutes, and allowed to react at room temperature for 3 hours. Thereafter, the reaction solution was filtered, and by concentrating the filtrate, A crude material of 2-hydroxy-2-methyl-1- (4- (2 - ((tetrahydro-2H- pyran-2-yl) oxy) ethoxy) phenyl) propan-1-one, was obtained (green liquid, 73.7 g).

Reference： [1]Patent: KR2017/125923,2017,A .Location in patent: Paragraph 0410-0413

40
[ 110-87-2 ]
[ 106797-53-9 ]
2-methoxy-2-methyl-1-(4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)propan-1-one [ No CAS ]

Reference： [1]Patent: KR2017/125923,2017,A

41
[ 70-34-8 ]
[ 106797-53-9 ]
1-{4-[2-(2,4-diaminophenoxy)ethoxy]phenyl}-2-hydroxy-2-methylpropan-1-one [ No CAS ]

Reference： [1]Patent: KR2017/125923,2017,A

42
[ 70-34-8 ]
[ 106797-53-9 ]
1-{4-[2-(2,4-dinitrophenoxy)ethoxy]phenyl}-2-hydroxy-2-methylpropan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In tetrahydrofuran; for 24h;Reflux; Inert atmosphere;	00 g ([Mw: 186.10 g / mol], 0.538 mol) of 2,4-dinitrofluorobenzene was added to a 2 L four-necked flask equipped with a stirrer and a nitrogen inlet tube,120.6 g of 2-hydroxy-4 '- (2-hydroxyethoxy) -2-methylpropiophenone([Mw: 224.25 g / mol], 0.538 mol),81.7 g ([Mw: 101.19 g / mol], 0.807 mol) of triethylamine,1000 g of THF was added,And refluxed for 24 hours. After completion of the reaction,The mixture was concentrated using a rotary evaporator,Ethyl acetate was added,This was washed several times with pure water and physiological saline,And dried over anhydrous magnesium sulfate.The crude product was recrystallized from ethyl acetate and normal hexane to obtain 157.0 g ([Mw: 390.34 g / mol], 0.402 mol, yield: 75%) of milky white powder. ). The nuclear magnetic resonance spectrum (1H-NMR spectrum) of hydrogen atoms in the molecule was confirmed. Measurement data is shown below.

Reference： [1]Patent: KR2017/125923,2017,A .Location in patent: Paragraph 0396-0401

43
3-[(3-{2,2-bis[({3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propanoyl}oxy)methyl]butoxy}-3-oxopropyl)sulfanyl]propanoic acid [ No CAS ]
[ 106797-53-9 ]
2-[({3-[(3-{2-[4-(2-hydroxy-2-methylpropanoyl)phenoxy]ethoxy}-3-oxopropyl)sulfanyl]propanoyl}oxy)methyl]-2-[({3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propanoyl}oxy)methyl]butyl 3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 25℃; for 28h;	Then, 0.31 g (0.0014 mol) of 2-hydroxy-1-[4-(2-hydroxy ethoxy) phenyl]-2-methylpropane-1-ON and 5 mL of acetonitrile were taught to a 100-mL four mouth flask, and it agitated at 25 degrees C. There The 3-(2-{-bis [3-(2-oxo 1,2-diphenylethyl sulfanil) propyonyloxymethyl] 2,2 butoxycarbonyl} ethylsulfanil) propionic acid 1.0g (0.0012 mol), The mixed solution of 0.27 g (0.0014 mol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochlorides, 0.020 g (0.00016 mol) of 4-dimethylaminopyridine, and 20 mL of acetonitrile was dropped. It was made to react at 25 degrees C after the end of dropping for 28 hours. It extracted by adding water and ethyl acetate after ending reaction. Condense the organic layer isolated preparatively and silica gel column chromatography refines the acquired concentrate, 3- of the viscous liquid of thin yellow. (2-oxo 1,2-diphenylethyl sulfanil) Propionic acid 2-[3-(2-{2-[4-(2-hydroxy-2-methylpropionyl) phenoxy] ethoxycarbonyl} ethylsulfanil) propyonyloxymethyl]-2-[3-. (2-oxo 1,2-diphenylethyl sulfanil) Propionyloxime ethyl] butyl was acquired.Acquired 3-. (2-oxo 1,2-diphenylethyl sulfanil) Propionic acid 2-[3-(2-{2-[4-(2-hydroxy-2-methylpropionyl) phenoxy] ethoxycarbonyl} ethylsulfanil) propyonyloxymethyl]-2-[3-. (2-oxo 1,2-diphenylethyl sulfanil) The quantity of propionyloxime ethyl] butyl was 0.30g, yield was 24% and the overall yield was 2.6%.

Reference： [1]Patent: JP2018/24627,2018,A .Location in patent: Paragraph 0152; 0155

44
[ 126235-57-2 ]
[ 106797-53-9 ]
2-{4-[2-methyl-2-({3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propanoyl}oxy)propanoyl]phenoxy}ethyl 3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		(0.0067 mol) of 3- (2-oxo-1,2-diphenylethylsulfanyl) propionic acid 2.9 g (24.4 mol) of thionyl chloride and 30 mL of toluene were placed in a 200 mL four-necked flask, At room temperature for 1.5 hours.After completion of the reaction, the reaction solution was concentrated, charged with 20 mL of dichloromethane,0.70 g (0.0031 mol) of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-0.63 g (0.0080 mol) of pyridine,0.10 g (0.0008 mol) of 4-dimethylaminopyridine,1.0 g (0.0010 mol) of triethylamine was added dropwise,And the mixture was heated and stirred under reflux.After completion of the reaction, water and ethyl acetate were added and extraction was carried out. The fractionated organic layer was concentrated and the obtained concentrated solution was purified by silica gel column chromatography to obtain 3- (2-oxo-1,2-diphenylethylsulfanyl) propionic acid 2- (4- {2 -methyl-2- [3- (2-oxo-1,2-diphenylethylsulfanyl) propionyloxy] propionyl} phenoxy) ethyl.The obtained 2- (4- {2-methyl-2- [3- (2-oxo-1,2-diphenylethylsulfanyl) propionyloxy] Propionyl} phenoxy) ethyl was 0.60 g, the yield was 20%, and the total yield was 18%.

Reference： [1]Patent: JP2018/24627,2018,A .Location in patent: Paragraph 0145-0147

45
[ 126235-57-2 ]
[ 106797-53-9 ]
2-[4-(2-hydroxy-2-methylpropanoyl)phenoxy]ethyl 3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 25℃; for 15h;Cooling with ice;	Subsequently, in a 200 mL four-necked flask,2.0 g (0.0067 mol) of 3- (2-oxo-1,2-diphenylethylsulfanyl) propionic acid,1.4 g (0.0073 mol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride,0.1 g (0.0008 mol) of 4-dimethylaminopyridine and 25 mL of acetonitrile, and the mixture was stirred under ice cooling.A mixed solution of 2.2 g (0.0098 mol) of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one and 30 mL of acetonitrile was added dropwise thereto.After completion of the dropwise addition, reaction was carried out at 25 C. for 15 hours.After completion of the reaction, water and ethyl acetate were added and extraction was carried out.The fractionated organic layer was concentrated and the obtained concentrated solution was purified by silica gel column chromatography to obtain 3- (2-oxo-1,2-diphenylethylsulfanyl) propionic acid 2- [ 2- (2-hydroxy-2-methylpropionyl) phenoxy] ethyl was obtained.The amount of 2- [4- (2-hydroxy-2-methylpropionyl) phenoxy] ethyl 3- (2-oxo-1,2-diphenylethylsulfanyl) propionate was 2.1 g and the yield was 62 %, The total yield was 44%.

Reference： [1]Patent: JP2018/24627,2018,A .Location in patent: Paragraph 0124; 0127

46
[ 27823-10-5 ]
[ 106797-53-9 ]
2-[4-(2-hydroxy-2-methylpropanoyl)phenoxy]ethyl 2-[(2-oxo-1,2-diphenylethyl)sulfanyl]acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 25℃; for 1h;	Subsequently, in a 100 mL four-necked flask,(0.0066 mol) of (2-oxo-1,2-diphenylethylsulfanyl) acetic acid,1.0 g (0.0061 mol) of 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-(0.0073 mol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 0.1 g (0.0008 mol) of 4-dimethylaminopyridine and 20 mL of acetonitrile and reacted at 25 C. for 1 hour .After completion of the reaction, water and ethyl acetate were added and extraction was carried out.The separated organic layer was concentrated, and the obtained concentrated solution was purified by silica gel column chromatography to obtain a pale yellow viscous liquid(2-oxo-1,2-diphenylethylsulfanyl)2- [4- (2-hydroxy-2-methylpropionyl) phenoxy] ethyl acetate was obtained.The amount of 2- (4- (2-hydroxy-2-methylpropionyl) phenoxy] ethyl acetate obtained was 0.80 g, the yield was 27%, the total The yield was 22%.

Reference： [1]Patent: JP2018/24627,2018,A .Location in patent: Paragraph 0137; 0140

47
[ 106797-53-9 ]
C₂₈H₂₉NO₅ [ No CAS ]

Reference： [1]Patent: CN107868034,2018,A

48
[ 1311403-44-7 ]
[ 106797-53-9 ]
C₁₈H₁₅S⁽¹⁺⁾*C₁₄H₁₅F₂O₈S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; at 23℃; for 12h;	4.6 parts of the compound represented by the formula (I-2-d) was added to the resulting solution containing the salt represented by the formula (I-2-c), and the mixture was stirred at 23 C. for 12 hours. To the obtained mixture, ion exchanged water 30 part was added and the mixture was stirred at 23 C. for 30 minutes, separated, and the organic layer was taken out. This operation was repeated 6 times. The obtained organic layer was concentrated to obtain 11.92 parts of a salt represented by the formula (I-2).

Reference： [1]Patent: JP2018/70596,2018,A .Location in patent: Paragraph 0247

49
[ 106797-53-9 ]
C₄₂H₅₈O₁₄ [ No CAS ]

Reference： [1]Patent: US2018/148519,2018,A1

50
[ 106797-53-9 ]
C₁₄H₂₀O₅ [ No CAS ]

Reference： [1]Patent: US2018/148519,2018,A1

51
[ 124-63-0 ]
[ 106797-53-9 ]
methanesulfonic acid 2-[4-(2-hydroxy-2-methyl-1-oxopropyl)phenoxy]ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 3h;	By the synthesis method described below, a photopolymerization initiator composition (I-1) as a type of photopolymerization initiator composition represented by General Formula (I) was obtained. (0190) First, 1.1 moles of a triethylantine solution dissolved in 500 ml of tetrahydrofuran was added dropwise to a mixture of 1 moles of Irgacure 2959 (trade name, manufactured by BASF SE) and 0.66 moles of methansulfonic acid chloride at room temperature, thereby obtaining a reaction mixture. (0191) The reaction mixture was stirred for 3 hours, and diluted with 500 ml of water and then with 300 ml of methyl ethyl ketone. By evaporating the solvents, a crude product was obtained, and the crude product was recrystallized from isopropanol, thereby obtaining 4-(2-methylsulfonyloxyethoxy)-phenyl-2-hydroxy-2-propylketone. By adding 90 ml of ethylene glycol containing 2.4 g of sodium (0.099 atomic equivalent) thereto, a suspension was obtained. (0192) The obtained suspension was heated for 2 hours at 40 C., and 0.09 moles of 4-(2-methylsulfonyloxyethoxy)-phenyl-2-hydroxy-2-propylketone was added to the solution. The mixture was heated for 2 hours at a temperature of 70 C. to 80 C., then diluted with 50 ml of water, and subjected to extraction using diethyl ether. The solvents were evaporated, and then the obtained crude product was purified by flash chromatography (silica gel, eluent: ethyl acetate), thereby obtaining the photopolymerization initiator (I-1) (Formula (I-1)) as an oily substance.

Reference： [1]Patent: US2018/148519,2018,A1 .Location in patent: Paragraph 0188-0192

52
[ 140-29-4 ]
[ 106797-53-9 ]
4-(4-(2-hydroxyethoxy)phenyl)-5,5-dimethyl-3-phenylfuran-2(5H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 11926 - 11935

53
[ 106797-53-9 ]
1-[p-(2-aminoethoxy)phenyl]-2-hydroxy-2-methyl-1-propanone hydrochloride [ No CAS ]