1-Chloro-1,1,3,3,3-pentafluoro-2-propanone → 1-(1,1,1,2,3,3-Hexafluoro-3-chloro-2-propoxy)-pentafluoro-2-propene

Temperature

25 °C

A suspension of potassium fluoride (5.80 g, 0.10 mol) and diglyme (100 ml) was stirred at 20° C. in a cooling bath while chloropentafluoroacetone (18.3 g, 0.10 mol) was distilled in. After the potassium fluoride had dissolved, perfluoroallyl fluorosulfate (23.0 g, 0.10 mol) was added rapidly with cooling of the reaction mixture. The resulting exothermic reaction was accompanied by the precipitation of solid. The mixture was stirred at 25° C. for one hour, and then the volatile components were transferred to a trap cooled to -80° C. by heating the reaction mixture at 42° C. (5 mm Hg). The volatile product was distilled from phosphorus pentoxide to give 1-(1,1,1,2,3,3-hexafluoro-3-chloro-2-propoxy)-pentafluoro-2-propene, (19.6 g, 0.059 mol, 59%) bp 85°-86° C. which was characterized by: λmax 5.55 (CF=CF2) and 7-10 μm (CF, C--O); 19F NMR, -68.6 (m) 2F, CF2Cl, -69.1 (m) 2F, CF2O, -78.8 (m) 3F, CF3, -93.2 (d J=54.7 Hz, each member d J=39.8 Hz, t J=7.5 Hz), 1F, cis--CF2 --CF=CF, -105.9 (d J=116.7 Hz, each member, d J=54.7 Hz, t J=24.0 Hz) 1F, trans-CF2 --CF=CF, -141.2 (t J=22.8 Hz, each member m) 1F, CF, and -190.4 ppm (d J=116.7 Hz, each member d J=39.8 Hz, t J=13.4 Hz) 1F, --CF2CF=C.

1. distillationwas distilled in
2. dissolutionAfter the potassium fluoride had dissolved
3. temperaturewith cooling of the reaction mixture
4. customThe resulting exothermic reaction
5. customwas accompanied by the precipitation of solid
6. customthe volatile components were transferred to a trap
7. temperaturecooled to -80° C.
8. temperatureby heating the reaction mixture at 42° C. (5 mm Hg)
9. distillationThe volatile product was distilled from phosphorus pentoxide

ORD record

ord-ea4972ea6c124a65b29f7a774bc15151

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04273728