Ethylene Glycol → HCID 18931708, compound

HRID 1599195Notes

Reaction equation

HRID 1599195 reaction equation
[Cl:1][C:2](=[C:7](Cl)[C:8]([F:11])([F:10])[F:9])[C:3]([F:6])([F:5])[F:4].C1(C)C=CC=CC=1.[CH2:20]([OH:23])[CH2:21][OH:22].[H-].[Na+]>O>[Cl:1][CH:2]([C:7]1([O:23][CH2:20][CH2:21][O:22]1)[C:8]([F:11])([F:10])[F:9])[C:3]([F:6])([F:5])[F:4]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 93372,3-Dichloro-1,1,1,4,4,4-hexafluorobut-2-eneHCID 24758Sodium hydride

Product 1

HCID 18931708HCID 18931708, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

233 g of 2,3-dichloro-1,1,1,4,4,4-hexafluorobut-2-ene were added dropwise to 400 ml of toluene, 80 g of ethylene glycol and 80 g of 60% strength sodium hydride in mineral oil at room temperature. The reaction mixture was stirred at 40° C. for 5 hours and water was then added. The organic phase was separated off, the aqueous phase was extracted with methyl t-butyl ether and the combined organic phases were dried over sodium sulfate. After removal of the solvent and subsequent distillation in vacuo, 180 g of 2-chloro-1,1,1,4,4,4-hexafluoro-3,3-ethylenedioxybutane (boiling point: 48° C./16 mbar) were obtained.

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was extracted with methyl t-butyl ether
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customAfter removal of the solvent and subsequent distillation in vacuo

Sources & evidence

ORD record
ord-d4861e87d1fb4e5899f279b4fcc07c64
Source dataset
uspto-grants-1998_04
Patent number
US05739394

Reaction notes

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