Diethyl Ether → Diphenyl Ether

HRID 34431Notes

Reaction equation

HRID 34431 reaction equation
[C:1]([OH:7])([C:3](F)(F)F)=O.[C@@H:8]1(O)[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1O.C(O[C:20]([CH3:22])=[CH2:21])(C)=C.[CH3:23]COCC>CC(C)=O>[C:8]1([O:7][C:1]2[CH:3]=[CH:21][CH:20]=[CH:22][CH:23]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acid2×HCID 92886trans-1,2-CyclohexanediolHCID 13483800Bisisopropenyl ether2×

Product 1

HCID 7583Diphenyl EtherYield 22%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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##

Workup

  1. waitThe reaction was completed after another hour
  2. customthe solvent evaporated under reduced pressure
  3. temperatureThe crude liquid was chilled
  4. filtrationfiltered
  5. distillationVacuum distillation at 21-24 mm Hg (2.8-3.2 kPa) in the presence of diphenyl ether as a high boiling solvent

Sources & evidence

ORD record
ord-2bad86edf459418f86547d0cfcd7adab
Source dataset
uspto-grants-1988_08
Patent number
US04761491

Reaction notes

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