Sulfuric Acid → 1,1,1,5,5,5-Hexafluoropentan-3-one

HRID 1421117Notes

Reaction equation

HRID 1421117 reaction equation
COC=C.C[O:6][C:7]([CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:8][C:9]([F:12])([F:11])[F:10].OS(O)(=O)=O>O>[F:10][C:9]([F:11])([F:12])[CH2:8][C:7](=[O:6])[CH2:13][C:14]([F:16])([F:17])[F:15]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7861Methyl vinyl etherHCID 54169582HCID 54169582, compound

Product 1

HCID 106316431,1,1,5,5,5-Hexafluoropentan-3-oneYield 77.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The vinyl methyl ether, 3-methoxy-1,1,1,5,5,5-hexafluoropent-2-ene, (21.3 g, 102 mmol) was added to 20 mL (36 g) concentrated H2SO4 at 15-20° C. over 15 min Stirring was continued for 10 min. and the reaction mixture poured into 100 mL cold water. The product was extracted with 2×40 mL ether. The combined extracts were washed with brine, dried (Na2SO4) and distilled to give 15.3 g (77% yield) of 1,1,1,5,5,5-hexafluoropentan-3-one, bp 122-123° C.

Workup

  1. extractionThe product was extracted with 2×40 mL ether
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. distillationdistilled

Sources & evidence

ORD record
ord-ae5047fdaa5f406a8b0172e84cd8ea5f
Source dataset
uspto-grants-2000_06
Patent number
US06072088

Reaction notes

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