Diethylene glycol diethyl ether → Difluoromethyl 1,1,2,3,3-pentafluoro-2-propyl ether

HRID 267648

Reaction equation

HRID 267648 reaction equation
Cl[C:2]([F:14])([F:13])[C:3]([O:9][CH:10]([F:12])[F:11])([F:8])[C:4](Cl)([F:6])[F:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCCOCCOCC)C>>[F:6][CH:4]([F:5])[C:3]([O:9][CH:10]([F:12])[F:11])([F:8])[CH:2]([F:14])[F:13]

Participants

4

Reactant 3

HCID 8179Diethylene glycol diethyl etherHCID 21226445Aluminium lithium hydrideHCID 86733856Difluoromethyl 1,3-dichloro-1,1,2,3,3-pentafluoro-2-propyl ether

Product 1

HCID 57127931Difluoromethyl 1,1,2,3,3-pentafluoro-2-propyl ether

Procedure

The ether XXVI (213 g, 0.79 mole) at 25°C was stirred as 0.9 M lithium aluminum hydride in diethylene glycol diethyl ether (484 ml, 0.436 mole of Li Al H4) was added dropwise. Then the product was distilled at atmospheric pressure through a cold water condensor into an ice cooled receiver until 157 g of IV was collected. This distillate was fractionally distilled to give IV, b760 68.1°-68.2°C, of 99.7% purity (by gas-liquid chromatography) in 93% of the theoretical yield; density at 23°C was 1.554. The structure of IV was confirmed by proton NMR spectroscopy.

Workup

  1. additionwas added dropwise
  2. distillationThen the product was distilled at atmospheric pressure through a cold water condensor into an ice cooled receiver until 157 g of IV
  3. customwas collected
  4. distillationThis distillate was fractionally distilled

Sources & evidence

ORD record
ord-7e033ab4bb6947abb95373d8b210fe2b
Source dataset
uspto-grants-1976_03
Patent number
US03943256

Linked notes

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