1,1,1,3,3,3-hexafluoropropan-2-one;hydrate

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At room temperature, 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed, and 0.5 g of p-toluenesulfonic acid monohydrate was added. The reaction solution was stirred and heated to 100° C. After the loss of the starting material was confirmed through TLC, ethyl acetate and an aqueous solution of 1N sodium hydroxide were added to the reaction solution, and phase separation was carried out. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed by addition of hexane. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 24.3 g (yield 69%) of the title compound as a powder form. The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure the residue was washed by addition of hexane The suspension was filtered thus obtained filtered residue was dried under reduced pressure at room temperature

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At room temperature, 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed, and 0.5 g of p-toluenesulfonic acid monohydrate was added. The reaction solution was stirred and heated to 100° C. After the loss of the starting material was confirmed through TLC, ethyl acetate and an aqueous solution of 1N sodium hydroxide were added to the reaction solution, and phase separation was carried out. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed by addition of hexane. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 24.3 g (yield 69%) of the title compound as a powder form. The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure the residue was washed by addition of hexane The suspension was filtered thus obtained filtered residue was dried under reduced pressure at room temperature

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100° C. for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a 1N sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid. was returned to room temperature washed with a 1N sodium hydroxide aqueous solution Then, the solvent was distilled off under reduced pressure the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100° C. for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a 1N sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid. was returned to room temperature washed with a 1N sodium hydroxide aqueous solution Then, the solvent was distilled off under reduced pressure the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100° C. for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a 1N sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid. was returned to room temperature washed with a 1N sodium hydroxide aqueous solution Then, the solvent was distilled off under reduced pressure the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100° C. for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a 1N sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid. was returned to room temperature washed with a 1N sodium hydroxide aqueous solution Then, the solvent was distilled off under reduced pressure the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At room temperature, 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed, and 0.5 g of p-toluenesulfonic acid monohydrate was added. The reaction solution was stirred and heated to 100° C. After the loss of the starting material was confirmed through TLC, ethyl acetate and an aqueous solution of 1N sodium hydroxide were added to the reaction solution, and phase separation was carried out. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed by addition of hexane. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 24.3 g (yield 69%) of the title compound as a powder form. The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure the residue was washed by addition of hexane The suspension was filtered thus obtained filtered residue was dried under reduced pressure at room temperature

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At room temperature, 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed, and 0.5 g of p-toluenesulfonic acid monohydrate was added. The reaction solution was stirred and heated to 100° C. After the loss of the starting material was confirmed through TLC, ethyl acetate and an aqueous solution of 1N sodium hydroxide were added to the reaction solution, and phase separation was carried out. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed by addition of hexane. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 24.3 g (yield 69%) of the title compound as a powder form. The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure the residue was washed by addition of hexane The suspension was filtered thus obtained filtered residue was dried under reduced pressure at room temperature

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

実験手順: To a solution of hexafluoroacetone trihydrate (0.42 mL, 3.0 mmol) in Et2O (3 mL) was added DBU (0.5 mL, 3.3 mmol). A white precipitate formed that was filtered, washed with Et2O (3×2 mL), and dried to provide hexafluoroacetone hydrate salt as a white solid (892.4 mg) in 89% yield. Recrystallization from Et2O/acetonitrile (slow evaporation) provided a crystalline solid suitable for X-ray structure analysis. 1H NMR (500 MHz, CD3CN) δ 10.20 (bs, 2H), 3.44 (m, 2H), 3.39 (t, 6 Hz, 2H), 3.22 (t, 6 Hz, 2H), 2.76 (m, 2H), 1.90 (m, 2H), 1.70 (m, 2H), 1.64 (m, 4H); 13C NMR (125 MHz, CD3CN) δ 166.6, 125.0 (q, J=294.4 Hz, 1C), 96.0 (m, 2C), 54.4, 49.1, 38.7, 32.1, 29.7, 27.4, 24.9, 20.3; 19F NMR (282 MHz, CD3CN) δ −83.2. A white precipitate formed that was filtered washed with Et2O (3×2 mL) dried

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At room temperature, 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed, and 0.5 g of p-toluenesulfonic acid monohydrate was added. The reaction solution was stirred and heated to 100° C. After the loss of the starting material was confirmed through TLC, ethyl acetate and an aqueous solution of 1N sodium hydroxide were added to the reaction solution, and phase separation was carried out. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed by addition of hexane. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 24.3 g (yield 69%) of the title compound as a powder form. The organic layer was dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure the residue was washed by addition of hexane The suspension was filtered thus obtained filtered residue was dried under reduced pressure at room temperature

反応条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 50-ml three-necked flask were placed 7.59 g (17.2 mmol) of the aqueous 56.8% potassium 3,3,3-trifluoro-2-trifluoromethyl-2-hydroxypropionate solution prepared in Reference Example 1 and 4.98 g (36 mmol) of potassium carbonate. 25 g of water was added to dissolve the mixture. The pH was 13. 5.75 g (36 mmol) of bromine was added dropwise over 60 minutes while stirring the mixture under heat at 40° C. in a water bath. After the completion of dropwise addition, the reaction was further performed at the same temperature for 3 hours, and the reaction was complete. The pH when the reaction was complete was 7 to 8. Hexafluoroacetone hydrate was obtained at a starting material conversion of 64% with a selectivity of 99% or higher. In a 50-ml three-necked flask were placed to dissolve the mixture After the completion of dropwise addition

反応条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 100-ml three-necked flask was placed 6.52 g (14.8 mmol) of the 56.8% aqueous potassium 3,3,3-trifluoro-2-trifluoromethyl-2-hydroxypropionate solution prepared in Reference Example 1. To this mixture were added 1.7 g of 35% hydrochloric acid and 0.8 g of potassium hydrogencarbonate in this order, thereby adjusting the pH to 8. Subsequently, 24.0 g (32.3 mmol) of 10% aqueous sodium hypochlorite solution was added over one hour while heating the mixture at 40° C. in a water bath, followed by further stirring for 5 hours while maintaining the same temperature. The pH when the reaction was complete was 8. Hexafluoroacetone hydrate was obtained at a starting material conversion of 90% with a selectivity of at least 99%. In a 100-ml three-necked flask was placed while maintaining the same temperature