Water → 2,2,3,4,4,4-Hexafluorobutyl 2,3-difluoropropanoate

HRID 1460848Notes

Reaction equation

HRID 1460848 reaction equation
[F:1][CH:2]([CH2:6][F:7])[C:3](Cl)=[O:4].[F:8][C:9]([F:18])([CH:12]([F:17])[C:13]([F:16])([F:15])[F:14])[CH2:10][OH:11].N1C=CC=CC=1.O>ClC(Cl)(Cl)Cl>[F:1][CH:2]([CH2:6][F:7])[C:3]([O:11][CH2:10][C:9]([F:8])([F:18])[CH:12]([F:17])[C:13]([F:15])([F:16])[F:14])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 5339902,2,3,4,4,4-Hexafluorobutan-1-olHCID 137815992,3-Difluoropropanoyl chloride

Product 1

HCID 147165092,2,3,4,4,4-Hexafluorobutyl 2,3-difluoropropanoateYield 75.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

34.6 g (0.27 mole) of 2,3-difluoropropanoyl chloride were added dropwise to a solution of 50 g (0.27 mole) of 2,2,3,4,4,4-hexafluoro-1-butanol and 21.6 g (0.27 mole) of pyridine in 200 ml of dry tetrachloromethane. Stirring was continued for a further 1 hour and then the mixture was poured into water, extracted, dried and distilled. In this manner, 56 g of 2,2,3,4,4,4-hexafluorobutyl 2,3-difluoropropionate were obtained having a melting point of 84° to 86° C. at 20 mbar. The purity of the product prepared was 95% (determined by gas chromatography).

Workup

  1. extractionextracted
  2. customdried
  3. distillationdistilled

Sources & evidence

ORD record
ord-216ceeaf2f7844a697e7823c1767e697
Source dataset
uspto-grants-1991_12
Patent number
US05072030

Reaction notes

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