Phenol → 2,2'-Bis(1,3-dioxolane)

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A suspension of 24.0 g (0.50 mol) of 50% NaH in mineral oil in 100 mL of diglyme was treated with a solution of 47.0 g (0.50 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 53.8 g (0.25 mol) of bis(2-chloroethyl) oxalate and 50 g (0.50 mol) of tetrafluoroethylene. The resulting reaction mixture was agitated for 12 hr, and then shaken with 1 L of cold water, after which layers formed. The lower layer, which was a mixture of solid and oil, was dissolved in 900 mL of ether to give an ether solution which was dried over CaSO4, filtered, and concentrated to 200 mL. Addition of 50 mL of petroleum ether to the concentrated ether solution caused precipitation of a crystalline product which was filtered off and rinsed to give 59.1 g of crystalline 2,2'-bi(2-[ 2-phenoxytetrafluoroethyl[-1,3-dioxolane), m.p. 102°-103°. The filtrate was cooled to obtain a second crop of crystals, m.p. 92°-97°, to give a total of 64.5 g (49% yield) of the bisketal. An analytical sample , m.p. 102.5°-103.5°, was obtained by recrystallization of some of the product from tetrahydrofuran/petroleum ether mixed solvent. The IR (KBr) and NMR (acetone-d6) spectra of the product were consistent with the structure. Anal.: Calcd for C22H18F8O6 : C, 49.82; H, 3.42; F, 28.66. Found C, 50.02; H, 3.47; F, 28.68.

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