Phenol → 2-(2-Phenoxytetrafluoro-ethyl)-1,3-dioxolane

Participants

Reaction Steps

A suspension of 17.3 g (0.36 mol) of 50% NaH in mineral oil in 100 mL of diglyme was treated with a solution of 33.9 g (0.36 mol) of phenol in 50 mL of diglyme. The resulting mixture was stirred overnight and then charged into a 400 mL metal tube along with 38.6 g (0.36 mol) of 2-chloroethyl formate and 40 g (0.40 mol) of tetrafluoroethylene. The resulting mixture was agitated for 12 h, and then added to 1 L of cold water, thereby causing the formation of layers. The lower layer was washed with water, dried over CaSO4, and distilled to afford 54.5 g (57% yield) of 2-(2-phenoxytetrafluoro-ethyl)-1,3-dioxolane, b.p. 62°-65° at 8 Pa (0.06 mm). The IR (neat) and NMR (CCl4) spectra of the product were consistent with the assigned structure. Anal.: Calcd. for C11H10F4O3 : C, 49.63; H, 3.79; F, 28.55. Found: C, 49.90; H, 3.80; F, 28.91.

Provenance & Evidence