Tetrafluoroethylene → 2-(1,1,2,2,2-Pentafluoroethyl)-2-(trifluoromethyl)-1,3-dioxolane

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Reaction Steps

A mixture of 29.1 g (0.50 mol) of dry potassium fluoride, 88.3 g (0.50 mol) of 2-chloroethyl trifluoroacetate, 150 mL of dimethylsulfoxide, and 50 g (0.50 mol) of tetrafluoroethylene was shaken in a 400-mL metal tube at 75° for 18 h. Volatile products were transferred from the reaction mixture held at 43° (1.2 mm). These volatiles were stirred with 500 mL of 10% aqueous NaOH to remove unreacted ester and a small amount of dimethylsulfoxide, then fractionated to afford 61.6 g (47%) of 2-trifluoromethyl-2-pentafluoroethyl-1,3-dioxolane, b.p. 118°-120°. IR (CCl4) and NMR (CCl4) spectra for the product were consistent with the assigned structure.

Provenance & Evidence