diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Examples of commercially available radical photopolymerization initiator include IRGACURE 651 (2,2-dimethoxy-1,2-diphenyl ethane-1-on), IRGACURE 184 (1-hydroxycyclohexyl-phenyl-ketone), DAROCUR 1173 (2-hydroxy-2-methyl-1-phenyl-propane-1-on), IRGACURE 2959 (1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-on), IRGACURE 127 (2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propnyl)-benzyl]phenyl}-2-methyl-propane-1-on, IRGACURE 907 (2-methyl-1-(4-methyl thiophenyl)-2-morpholinopropane-1-on), IRGACURE 369 (2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1), IRGACURE 379 (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone), DAROCUR TPO (2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide), IRGACURE 819 (bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide), IRGACURE 784 (bis(eta-5-2,4-cyclopentadiene-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium), IRGACURE OXE 01 (1.2-octanedione, 1-[4-(phenylthio)-, 2-(o-benzoyloxime)]), IRGACURE OXE 02 (ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(o-acetyloxime)), and IRGACURE 754 (mixture of oxyphenyl acetic acid, 2-[2-oxo-2-phenylacetoxyethoxy]ethyl ester and oxyphenyl acetic acid, 2-(2-hydroxyethoxy)ethyl ester)(all produced by BASF); Speedcure TPO (produced by Lambson), KAYACURE DETX-S (2,4-diethylthioxantone) (produced by Nippon Kayaku Co., Ltd.); Lucirin TPO, LR8893, LR8970 (produced by BASF); Ubecryl P36 (produced by UCB), and the like. all produced by BASF)

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 648 parts of methoxydiphenylphosphine are added slowly to 547.5 parts of 2,4,6-trimethylbenzoyl chloride at 50°-95° C. in a stirred apparatus equipped with a reflux condenser and dropping funnel. The mixture is then stirred for 4-5 hours at 50° C., the contents of the flask are dissolved in ether at 30° C., and petroleum ether is added until the mixture starts to turn cloudy. On cooling, 910 parts (87% of theory) of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide crystallize. Pale yellow crystals, melting point 89°-92° C. equipped with a reflux condenser On cooling 910 parts (87% of theory) of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide crystallize

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Examples of commercially available radical photopolymerization initiator include IRGACURE 651 (2,2-dimethoxy-1,2-diphenyl ethane-1-on), IRGACURE 184 (1-hydroxycyclohexyl-phenyl-ketone), DAROCUR 1173 (2-hydroxy-2-methyl-1-phenyl-propane-1-on), IRGACURE 2959 (1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-on), IRGACURE 127 (2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propnyl)-benzyl]phenyl}-2-methyl-propane-1-on, IRGACURE 907 (2-methyl-1-(4-methyl thiophenyl)-2-morpholinopropane-1-on), IRGACURE 369 (2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1), IRGACURE 379 (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone), DAROCUR TPO (2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide), IRGACURE 819 (bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide), IRGACURE 784 (bis(eta-5-2,4-cyclopentadiene-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium), IRGACURE OXE 01 (1.2-octanedione, 1-[4-(phenylthio)-, 2-(o-benzoyloxime)]), IRGACURE OXE 02 (ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(o-acetyloxime)), and IRGACURE 754 (mixture of oxyphenyl acetic acid, 2-[2-oxo-2-phenylacetoxyethoxy]ethyl ester and oxyphenyl acetic acid, 2-(2-hydroxyethoxy)ethyl ester)(all produced by BASF); Speedcure TPO (produced by Lambson), KAYACURE DETX-S (2,4-diethylthioxantone) (produced by Nippon Kayaku Co., Ltd.); Lucirin TPO, LR8893, LR8970 (produced by BASF); Ubecryl P36 (produced by UCB), and the like. all produced by BASF)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Examples of commercially available radical photopolymerization initiator include IRGACURE 651 (2,2-dimethoxy-1,2-diphenyl ethane-1-on), IRGACURE 184 (1-hydroxycyclohexyl-phenyl-ketone), DAROCUR 1173 (2-hydroxy-2-methyl-1-phenyl-propane-1-on), IRGACURE 2959 (1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-on), IRGACURE 127 (2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propnyl)-benzyl]phenyl}-2-methyl-propane-1-on, IRGACURE 907 (2-methyl-1-(4-methyl thiophenyl)-2-morpholinopropane-1-on), IRGACURE 369 (2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1), IRGACURE 379 (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone), DAROCUR TPO (2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide), IRGACURE 819 (bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide), IRGACURE 784 (bis(eta-5-2,4-cyclopentadiene-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1-yl)-phenyl)titanium), IRGACURE OXE 01 (1.2-octanedione, 1-[4-(phenylthio)-, 2-(o-benzoyloxime)]), IRGACURE OXE 02 (ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(o-acetyloxime)), and IRGACURE 754 (mixture of oxyphenyl acetic acid, 2-[2-oxo-2-phenylacetoxyethoxy]ethyl ester and oxyphenyl acetic acid, 2-(2-hydroxyethoxy)ethyl ester)(all produced by BASF); Speedcure TPO (produced by Lambson), KAYACURE DETX-S (2,4-diethylthioxantone) (produced by Nippon Kayaku Co., Ltd.); Lucirin TPO, LR8893, LR8970 (produced by BASF); Ubecryl P36 (produced by UCB), and the like. all produced by BASF)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under argon and with exclusion of moisture, 2.76 g of lithium (0.40 mol) are suspended at room temperature in 100 ml of THF and this suspension is charged with 0.10 g (0.00078 mol) of naphthalene. This mixture is then stirred for 10 minutes at room temperature. With occasional cooling and vigorous stirring, 45.2 g (0.0 mol) of P-chlorodiphenyl phosphine are added dropwise to the dark brown suspension at 10–25° C. After stirring for 4 hours, the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and using argon as protective gas. 38.0 g (0.2 mol) of 2,4,6-trimethylbenzoyl chloride are added dropwise, with stirring and cooling, at 10–20° C. over 1 hour and the mixture is then stirred for another 30 minutes. The organic phase is concentrated by evaporation in a Rotavap and the residue is taken up in 100 ml of toluene and charged, with vigorous stirring at a temperature from 50–60° C., with 23.0 g (0.20 mol) of hydrogen peroxide (30%). The reaction is complete after stirring for 30 minutes. The reaction emulsion is poured on water and washed with an aqueous saturated sodium hydrogencarbonate solution and then dried over magnesium sulfate and filtered. The filtrate is concentrated by evaporation in a Rotavap. The residue is crystallised from petroleum ether/ethyl acetate and dried in a vacuum drying oven at 40° C., yielding 55.0 g (79% of theory) of the title compound in the form of a yellow powder having a melting point of 89–90° C. With occasional cooling After stirring for 4 hours the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and with stirring cooling, at 10–20° C. over 1 hour the mixture is then stirred for another 30 minutes The organic phase is concentrated by evaporation in a Rotavap charged after stirring for 30 minutes The reaction emulsion is poured on water washed with an aqueous saturated sodium hydrogencarbonate solution dried over magnesium sulfate filtered The filtrate is concentrated by evaporation in a Rotavap The residue is crystallised from petroleum ether/ethyl acetate dried in a vacuum drying oven at 40° C.

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under argon and with exclusion of moisture, 2.76 g of lithium (0.40 mol) are suspended at room temperature in 100 ml of THF and this suspension is charged with 0.10 g (0.00078 mol) of naphthalene. This mixture is then stirred for 10 minutes at room temperature. With occasional cooling and vigorous stirring, 45.2 g (0.0 mol) of P-chlorodiphenyl phosphine are added dropwise to the dark brown suspension at 10–25° C. After stirring for 4 hours, the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and using argon as protective gas. 38.0 g (0.2 mol) of 2,4,6-trimethylbenzoyl chloride are added dropwise, with stirring and cooling, at 10–20° C. over 1 hour and the mixture is then stirred for another 30 minutes. The organic phase is concentrated by evaporation in a Rotavap and the residue is taken up in 100 ml of toluene and charged, with vigorous stirring at a temperature from 50–60° C., with 23.0 g (0.20 mol) of hydrogen peroxide (30%). The reaction is complete after stirring for 30 minutes. The reaction emulsion is poured on water and washed with an aqueous saturated sodium hydrogencarbonate solution and then dried over magnesium sulfate and filtered. The filtrate is concentrated by evaporation in a Rotavap. The residue is crystallised from petroleum ether/ethyl acetate and dried in a vacuum drying oven at 40° C., yielding 55.0 g (79% of theory) of the title compound in the form of a yellow powder having a melting point of 89–90° C. With occasional cooling After stirring for 4 hours the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and with stirring cooling, at 10–20° C. over 1 hour the mixture is then stirred for another 30 minutes The organic phase is concentrated by evaporation in a Rotavap charged after stirring for 30 minutes The reaction emulsion is poured on water washed with an aqueous saturated sodium hydrogencarbonate solution dried over magnesium sulfate filtered The filtrate is concentrated by evaporation in a Rotavap The residue is crystallised from petroleum ether/ethyl acetate dried in a vacuum drying oven at 40° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 648 parts of methoxydiphenylphosphine are added slowly to 547.5 parts of 2,4,6-trimethylbenzoyl chloride at 50°-55° C. in a stirred apparatus equipped with a reflux condenser and dropping funnel. Stirring is continued for 4-5 hours at 50° C., the contents of the flask are dissolved in ether at 30° C., and petroleum ether is added until the mixture begins to turn cloudy. On cooling, 910 parts (87% of theory) of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide crystallize. Melting point: 80°-81° C. The product is in the form of pale yellow crystals. equipped with a reflux condenser On cooling 910 parts (87% of theory) of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide crystallize

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under argon and with exclusion of moisture, 2.76 g of lithium (0.40 mol) are suspended at room temperature in 100 ml of THF and this suspension is charged with 0.10 g (0.00078 mol) of naphthalene. This mixture is then stirred for 10 minutes at room temperature. With occasional cooling and vigorous stirring, 45.2 g (0.0 mol) of P-chlorodiphenyl phosphine are added dropwise to the dark brown suspension at 10-25° C. After stirring for 4 hours, the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and using argon as protective gas. 38.0 g (0.2 mol) of 2,4,6-trimethylbenzoyl chloride are added dropwise, with stirring and cooling, at 10-20° C. over 1 hour and the mixture is then stirred for another 30 minutes. The organic phase is concentrated by evaporation in a Rotavap and the residue is taken up in 100 ml of toluene and charged, with vigorous stirring at a temperature from 50-60° C., with 23.0 g (0.20 mol) of hydrogen peroxide (30%). The reaction is complete after stirring for 30 minutes. The reaction emulsion is poured on water and washed with an aqueous saturated sodium hydrogencarbonate solution and then dried over magnesium sulfate and filtered. The filtrate is concentrated by evaporation in a Rotavap. The residue is crystallised from petroleum ether/ethyl acetate and dried in a vacuum drying oven at 40° C., yielding 55.0 g (79% of theory) of the title compound in the form of a yellow powder having a melting point of 89-90° C. With occasional cooling After stirring for 4 hours the red solution is filtered via a glass frit (G2 porosity) into a sulfonation flask with exclusion of moisture and with stirring cooling, at 10-20° C. over 1 hour the mixture is then stirred for another 30 minutes The organic phase is concentrated by evaporation in a Rotavap charged after stirring for 30 minutes The reaction emulsion is poured on water washed with an aqueous saturated sodium hydrogencarbonate solution dried over magnesium sulfate filtered The filtrate is concentrated by evaporation in a Rotavap The residue is crystallised from petroleum ether/ethyl acetate dried in a vacuum drying oven at 40° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-hydroxycyclohexyl phenyl ketone; bis (2,4,6-trimethylbenzoyl)-phenylphosphine oxide such as Irgacure 819 from BASF; 2,2′-dimethoxy-2-phenylacetophenone; 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butanone; 2-methyl-1-(4(methylthio)phenyl)-2-moropholino-1-propane; bis (2,6-dimethoxybenzoyl)-2,4,4-trimethyl pentyl phosphine oxide; and 1-hydroxy-cyclohexyl-phenyl-ketone (a blend of 25:75 of the latter two components may be employed).

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 648 parts of methoxydiphenylphosphine are added slowly to 547.5 parts of 2,4,6-trimethylbenzoyl chloride at 50°-95° C. in a stirred apparatus equipped with a reflux condenser and dropping funnel. The mixture is then stirred for 4-5 hours at 50° C., the contents of the flask are dissolved in ether at 30° C., and petroleum ether is added until the mixture starts to turn cloudy. On cooling, 910 parts (87% of theory) of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide crystallize. Pale yellow crystals, melting point 89°-92° C. equipped with a reflux condenser On cooling 910 parts (87% of theory) of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide crystallize