Diethyl Ether → Diphenyl Ether

Participants

Reaction Steps

Three microliters (3.9×10-5 mole) of CF3COOH was added to trans-1,2-cyclohexanediol (2.88 g, 2.48×10-2 mole) and diisopropenyl ether (2.0 ml, 1.62×10-2 mole) dissolved in 25 ml of acetone at 50° C. After 11 minutes, 0.5 ml (4.05×10-3 mole) of diisopenpenyl ether and 3 μl (3.9×10-5 mole) of CF3COOH were added, followed 15 minutes later by 0.5 ml (4.05×10-3 mole) of diisopropenyl ether. The reaction was completed after another hour of stirring, and the solvent evaporated under reduced pressure. The crude liquid was chilled and filtered to remove 0.32 g (2.75×10-3 mole) of starting diol. Vacuum distillation at 21-24 mm Hg (2.8-3.2 kPa) in the presence of diphenyl ether as a high boiling solvent produced 1.93 g (92 percent product and 7.2 percent diphenyl ether; boiling point 84° C. to 85° C.) and 0.31 g (77 percent product and 22 percent diphenyl ether; boiling point 88° C. to 90° C.) of colorless liquid. The yield was 1.29×10-2 mole (52 percent). The product has a boiling point of 92° C. to 96° C. at 22 mm Hg (2.9 kPa). Nuclear magnetic resonance and mass spectrum analysis showed the product to have the structure: ##STR10##

Provenance & Evidence