Phenol → 2-Trifluoromethyl-2-(2-phenoxytetrafluoroethyl)-1,3-dioxolane

HRID 483891Notes

Reaction equation

HRID 483891 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:10][C:11]([F:19])([F:18])[C:12]([O:14][CH2:15][CH2:16]Cl)=[O:13].[F:20][C:21]([F:25])=[C:22]([F:24])[F:23]>COCCOCCOC.O>[F:10][C:11]([F:19])([F:18])[C:12]1([C:22]([F:24])([F:23])[C:21]([F:25])([F:20])[O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:14][CH2:15][CH2:16][O:13]1

Participants

7

Reactant 4

HCID 996PhenolHCID 8301TetrafluoroethyleneHCID 24758Sodium hydrideHCID 125747172-Chloroethyl trifluoroacetate

Product 1

HCID 144014492-Trifluoromethyl-2-(2-phenoxytetrafluoroethyl)-1,3-dioxolaneYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent2×

Procedure

A suspension of 12.0 g (0.25 mol) of 50% NaH in mineral oil in 100 mL of dry diglyme (diethylene glycol dimethyl ether) was stirred at 25° under nitrogen while a solution of 23.5 g (0.25 mol) of phenol in 50 mL of diglyme was added. The resulting mixture was stirred until evolution of gas ceased, then charged into a 400 mL metal tube along with 44.3 g (0.25 mol) of 2-chloroethyl trifluoroacetate and 40 g (0.70 mol) of tetrafluoroethylene. The resulting mixture was agitated for 6 h while the temperature rose to 34° and subsided. Next the mixture was heated at 50 ° for 6 h. The resulting reaction mixture was added to 1 L of water, thereby causing the formation of layers. The lower layer was separated, washed with water, dried over CaSO4, and distilled to give 61.2 g (73% yield) of 2-trifluoromethyl-2-(2-phenoxytetrafluoroethyl)-1,3-dioxolane, b.p. 64°-67° at 13 Pa (0.1 mm). The IR (CCl4) and NMR (CCl4) spectra of the product were consistent with the structure assignment. Anal.: Calcd. for C12H9F7O3 : C, 43.13; H, 2.71; F, 39.80. Found: C, 43.23; H, 2.75; F, 39.90.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was agitated for 6 h while the temperature
  3. customrose to 34°
  4. temperatureNext the mixture was heated at 50 ° for 6 h
  5. customThe resulting reaction mixture
  6. customThe lower layer was separated
  7. washwashed with water
  8. dry with materialdried over CaSO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-5e8d704770444c73848dd03ade382bf1
Source dataset
uspto-grants-1993_07
Patent number
US05227500

Reaction notes

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