Tetrafluoroethylene → 2-(1,1,2,2,2-Pentafluoroethyl)-2-(trifluoromethyl)-1,3-dioxolane

HRID 345620Notes

Reaction equation

HRID 345620 reaction equation
[F-:1].[K+].[F:3][C:4]([F:12])([F:11])[C:5]([O:7][CH2:8][CH2:9]Cl)=[O:6].[F:13][C:14]([F:18])=[C:15]([F:17])[F:16].[OH-].[Na+]>CS(C)=O>[F:3][C:4]([F:12])([F:11])[C:5]1([C:15]([F:17])([F:16])[C:14]([F:1])([F:18])[F:13])[O:7][CH2:8][CH2:9][O:6]1

Participants

6

Reactant 4

HCID 8301TetrafluoroethyleneHCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 125747172-Chloroethyl trifluoroacetate

Product 1

HCID 144014652-(1,1,2,2,2-Pentafluoroethyl)-2-(trifluoromethyl)-1,3-dioxolaneYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 29.1 g (0.50 mol) of dry potassium fluoride' 88.3 g (0.50 mol) of 2-chloroethyl trifluoroacetate, 150 mL of dimethylsulfoxide, and 50 g (0.50 mol) of tetrafluoroethylene was shaken in a 400-mL metal tube at 75° for 18 h. Volatile products were transferred from the reaction mixture held at 43° (1.2 mm). These volatiles were stirred with 500 mL of 10% aqueous NaOH to remove unreacted ester and a small amount of dimethylsulfoxide, then fractionated to afford 61.6 g (47%) of 2-trifluoromethyl-2-pentafluoroethyl-1,3-dioxolane, b.p. 118°-120° . IR (CCl4) and NMR (CCl4) spectra for the product were consistent with the assigned structure. Anal.: Calcd. for C6H4F8O2 : C, 27.71; H, 1.55; F, 58.44. Found: C, 27.57; H, 1.65; F, 58.40.

Workup

  1. customheld at 43°
  2. customto remove unreacted ester

Sources & evidence

ORD record
ord-8558ffafa0cb4fbaabe2a3ba82c1fff7
Source dataset
uspto-grants-1991_10
Patent number
US05057586

Reaction notes

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