1,1,1,3,3,3-hexafluoropropan-2-yl 2-fluoroprop-2-enoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-liter glass flask which had been equipped with a thermometer.- a stirrer, a reflux condenser and a dropping funnel was charged with 1.2 l of o-xylene, 29 g (0.4 mol) of dimethylformamide and 200 g (1.87 mol) of ammonium α-fluoroacrylate. To this initial charge were then added dropwise in the course of 1 hour 238 g (2.0 mol) of thionyl chloride. The reaction mixture was then maintained at a temperature of 80° C. for 2 hours. After subsequently cooling down to a temperature of 0° C., the mixture had added to it a mixture of 202 g (2 mol) of triethylamine and 336 g (2 mol) of hexafluoroisopropanol in the course of 30 minutes. The resulting mixture was stirred for a further 30 minutes, and the resulting precipitate was filtered off. The filtrate was treated with 1 g of hydroquinone monomethyl ether and rapidly distilled under a pressure of 266 mbar. The fraction obtained within the temperature range from 45° to 85° C. was washed with hydrochloric acid (2.4 molar) and with water, was dried and was distilled again, giving 232 g (52 percent of theory) of pure hexafluoroisopropyl α-fluoroacrylate. A 2-liter glass flask which had been equipped with a thermometer To this initial charge After subsequently cooling down to a temperature of 0° C. the mixture had added to it the resulting precipitate was filtered off The filtrate was treated with 1 g of hydroquinone monomethyl ether rapidly distilled under a pressure of 266 mbar The fraction obtained within the temperature range from 45° to 85° C. was washed with hydrochloric acid (2.4 molar) and with water was dried was distilled again

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12 g of 2-fluoroacryloyl chloride and 27 g of 1,1,1,3,3,3-hexafluoro-2-propanol were introduced into a round-bottomed flask placed in an ice bath. 16 g of triethylamine were added portionwise to the reaction mixture. After reacting for an additional 3 h, approximately 70 ml of water were added. The aqueous and organic phases were subsequently separated and the organic phase was analysed by GC. The conversion of the 1,1,1,3,3,3-hexafluoroisopropanol was 68%. The yield of ester, based on the amount of 2-fluoroacrylic acid employed in the first stage, was 66%. placed in an ice bath The aqueous and organic phases were subsequently separated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12 g of 2-fluoroacryloyl chloride and 27 g of 1,1,1,3,3,3-hexafluoro-2-propanol were introduced into a round-bottomed flask placed in an ice bath. 16 g of triethylamine were added portionwise to the reaction mixture. After reacting for an additional 3 h, approximately 70 ml of water were added. The aqueous and organic phases were subsequently separated and the organic phase was analysed by GC. The conversion of the 1,1,1,3,3,3-hexafluoroisopropanol was 68%. The yield of ester, based on the amount of 2-fluoroacrylic acid employed in the first stage, was 66%. placed in an ice bath The aqueous and organic phases were subsequently separated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-Liter glass flask which had been equipped with a thermometer, a stirrer, a reflux condenser and a dropping funnel was charged with 1.2 l of o-xylene, 29 g (0.4 mol) of dimethylformamide and 200 g (1.87 mol) of ammonium α-fluoroacrylate. To this initial charge were then added dropwise in the course of 1 hour 238 g (2.0 mol) of thionyl chloride. The reaction mixture was then maintained at a temperature of 80° C. for 2 hours. After subsequently cooling down to a temperature of 0° C., the mixture had added to it a mixture of 202 g (2 mol) of triethylamine and 336 g (2 mol) of hexafluoroisopropanol in the course of 30 minutes. The resulting mixture was stirred for a further 30 minutes, and the resulting precipitate was filtered off. The filtrate was treated with 1 g of hydroquinone monomethyl ether and rapidly distilled under a pressure of 266 mbar. The fraction obtained within the temperature range from 45° to 85° C. was washed with hydrochloric acid (2.4 molar) and with water, was dried and was distilled again, giving 232 g (52 percent of theory) of pure hexafluoroisopropyl α-fluoroacrylate. This ester was a colorless liquid with a refractive index nD23 =1.3145, a boiling point of 46.8° C. (at 213 mbar) and a density of 1.453 g/cm3 (at 25° C.). In the wavelength range from 380 to 680 nm this ester had an average transmission of more than 99 percent. A 2-Liter glass flask which had been equipped with a thermometer, a stirrer, a reflux condenser and a dropping funnel To this initial charge After subsequently cooling down to a temperature of 0° C. the mixture had added to it the resulting precipitate was filtered off The filtrate was treated with 1 g of hydroquinone monomethyl ether rapidly distilled under a pressure of 266 mbar The fraction obtained within the temperature range from 45° to 85° C. was washed with hydrochloric acid (2.4 molar) and with water was dried was distilled again

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 107 g (1 mol) of the ammonium salt of α-fluoroacrylic acid are mixed with 14.5 g (0.2 mol) of dimethylformamide and 0.6 liter of xylene, and 131 g (1.1 mol) of thionyl chloride are added dropwise to the mixture in the course of one hour; the mixture is then warmed at a temperature of 80° C. for two hours. After cooling to a temperature of 0° C., a mixture of 204 g (1.1 mol) of tributylamine and 185 g (1.1 mol) of hexafluoroisopropanol is added to the reaction mixture in the course of 30 minutes. The mixture is then stirred at a temperature of 30° C. for a further hour and is finally filtered. The filtrate is distilled under a pressure of 270 mbar and hexafluoroisopropyl α-fluoroacrylate is obtained as a colorless liquid. are added dropwise to the mixture in the course of one hour After cooling to a temperature of 0° C. is added to the reaction mixture in the course of 30 minutes is finally filtered The filtrate is distilled under a pressure of 270 mbar

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-liter glass flask which had been equipped with a thermometer.- a stirrer, a reflux condenser and a dropping funnel was charged with 1.2 l of o-xylene, 29 g (0.4 mol) of dimethylformamide and 200 g (1.87 mol) of ammonium α-fluoroacrylate. To this initial charge were then added dropwise in the course of 1 hour 238 g (2.0 mol) of thionyl chloride. The reaction mixture was then maintained at a temperature of 80° C. for 2 hours. After subsequently cooling down to a temperature of 0° C., the mixture had added to it a mixture of 202 g (2 mol) of triethylamine and 336 g (2 mol) of hexafluoroisopropanol in the course of 30 minutes. The resulting mixture was stirred for a further 30 minutes, and the resulting precipitate was filtered off. The filtrate was treated with 1 g of hydroquinone monomethyl ether and rapidly distilled under a pressure of 266 mbar. The fraction obtained within the temperature range from 45° to 85° C. was washed with hydrochloric acid (2.4 molar) and with water, was dried and was distilled again, giving 232 g (52 percent of theory) of pure hexafluoroisopropyl α-fluoroacrylate. A 2-liter glass flask which had been equipped with a thermometer To this initial charge After subsequently cooling down to a temperature of 0° C. the mixture had added to it the resulting precipitate was filtered off The filtrate was treated with 1 g of hydroquinone monomethyl ether rapidly distilled under a pressure of 266 mbar The fraction obtained within the temperature range from 45° to 85° C. was washed with hydrochloric acid (2.4 molar) and with water was dried was distilled again

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12 g of 2-fluoroacryloyl chloride and 27 g of 1,1,1,3,3,3-hexafluoro-2-propanol were introduced into a round-bottomed flask placed in an ice bath. 16 g of triethylamine were added portionwise to the reaction mixture. After reacting for an additional 3 h, approximately 70 ml of water were added. The aqueous and organic phases were subsequently separated and the organic phase was analysed by GC. The conversion of the 1,1,1,3,3,3-hexafluoroisopropanol was 68%. The yield of ester, based on the amount of 2-fluoroacrylic acid employed in the first stage, was 66%. placed in an ice bath The aqueous and organic phases were subsequently separated