Potassium Hydroxide → HCID 11022884, compound

Participants

Reaction Steps

In a flask was charged 2,2-bis(trifluoromethyl)-4,5-difluoro-4,5-di(2-iodoethyl)-1,3-dioxolane (95 g, 017 mole), KOH (189 ml 10M, 1.89 mole) and phase transfer catalyst (Note) (24.6 g as 60% w/w aqueous solution, 0.034 mole). The reaction mixture was vigorously stirred at ambient temperature for 4 hrs. The bottom organic layer was separated and was further purified by distillation giving 25.0 g (49.3% yield) of the desired product obtained as a clear, colorless liquid, bp. 90° C./200 mm Hg. This product is a trans/cis isomeric mixture. The trans and cis isomers could be separated by distillation on a spinning-band column. 1H NMR (CDCl3): δ 5.90 (m, 2H), 5.70 (m, 4H) (trans isomer); 5.76 (m, 4H), 5.58 (m, 2H) (cis isomer); 19F NMR (CDCl3): -80.2 (m, 6F), -109.6 (m, 2F) (trans isomer); -80.2 (m, 3F), -81.0 (q, J=8.6 Hz, 3F),-109.3 (quintet, J=7.0 Hz, 2F).

Provenance & Evidence