Trichloroacetic Acid → 2,2,3,3,4,4,5,5,6,6-Decafluoro-1-(trichloromethyl)-1-cyclohexanol

Temperature

-10 °C

A solution of 30 g of perfluorocyclohexanone and 31.7 g of trichloroacetic acid was stirred in a pre-dried reaction vessel containing 113 mL of hexamethylphosphoramide. This mixture was cooled to −10° C. in a dry ice/acetone bath. Slight gas evolution was noted before and during the ketone addition. The stirred milky white reaction mixture was maintained at about 0° C. for an hour and then allowed to warm to 23° C. and stirring was continued 17 hours. The clear yellow solution was quenched with 150 mL of 10% HCl and then transferred to a separatory funnel with 400 mL of ethyl ether. This organic phase was washed with 4×500 mL of dilute HCl and then 300 mL of saturated NaCl solution. The solvent was removed by evaporation. The residue (33.7 g) contained 40.8% product by GC, confirmed by fluorine NMR. This carbinol can be converted to the corresponding acrylate by methods previously described (cf. Example 24).

1. temperatureThe stirred milky white reaction mixture was maintained at about 0° C. for an hour
2. temperatureto warm to 23° C.
3. customThe clear yellow solution was quenched with 150 mL of 10% HCl
4. customtransferred to a separatory funnel with 400 mL of ethyl ether
5. washThis organic phase was washed with 4×500 mL of dilute HCl
6. customThe solvent was removed by evaporation

ORD record

ord-5c55fb8d56554b9a8804037f208ad620

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313245B1