Hydroquinone → 1,4-Bis(2,2,2-trifluoroethoxy)benzene

HRID 236073Notes

Reaction equation

HRID 236073 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].FC(F)(F)S([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])(=O)=O.[C:20]1([CH:27]=[CH:26][C:24](O)=[CH:23][CH:22]=1)O>CC(C)=O>[F:17][C:14]([F:15])([F:16])[CH2:13][O:12][C:20]1[CH:27]=[CH:26][C:24]([O:4][CH2:1][C:14]([F:17])([F:16])[F:15])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 7371561,4-Bis(2,2,2-trifluoroethoxy)benzeneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of 2.42 moles (334.4 g.) of potassium carbonate, 2.2 moles (510.6 g.) of 2,2,2-trifluoroethyl trifluoromethanesulfonate in 1.02 liters of acetone is added a solution of 1.0 mole (110 g.) of hydroquinone in 1.1 liters of acetone, slowly over a 2 hour period. The reaction is then heated at reflux for 24 hours, the reaction mixture is evaporated, and 2 liters of chloroform and 2 liters of water are added to the residue. The chloroform layer is separated, the aqueous layer is washed twice with 1 liter of chloroform, and the combined chloroform solution is washed with 1 liter of water. The chloroform solution is dried over magnesium sulfate, then concentrated under vacuum. Hexane is added to the residue and the solid product is collected by filtration and washed with hexane. Additional material is collected from the concentrated residues. A yield of 88 percent, 241 g. of 1,4-bis(2,2,2-trifluoroethoxy)benzene, m.p. 75°-77° C. is obtained.

Workup

  1. temperatureThe reaction is then heated
  2. temperatureat reflux for 24 hours
  3. customthe reaction mixture is evaporated
  4. addition2 liters of chloroform and 2 liters of water are added to the residue
  5. customThe chloroform layer is separated
  6. washthe aqueous layer is washed twice with 1 liter of chloroform
  7. washthe combined chloroform solution is washed with 1 liter of water
  8. dry with materialThe chloroform solution is dried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. additionHexane is added to the residue
  11. filtrationthe solid product is collected by filtration
  12. washwashed with hexane
  13. customAdditional material is collected from the concentrated residues

Sources & evidence

ORD record
ord-0c65e576f7e7433eacfd9b7e42b52547
Source dataset
uspto-grants-1987_02
Patent number
US04642384

Reaction notes

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