Acetic Acid → HCID 21703599, compound

HRID 650384Notes

Reaction equation

HRID 650384 reaction equation
[F:1][C:2]([F:13])([C:9]([F:12])([F:11])[F:10])[CH2:3][CH2:4][CH2:5][S:6][CH:7]=[CH2:8].OO.[OH2:16].C(O)(=[O:19])C>>[F:13][C:2]([F:1])([C:9]([F:10])([F:11])[F:12])[CH2:3][CH2:4][CH2:5][S:6]([CH:7]=[CH2:8])(=[O:19])=[O:16]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 21703614HCID 21703614, compound

Product 1

HCID 21703599HCID 21703599, compound

Conditions

Temperature
70 °C

Procedure

A solution of 34 g of (4,4,5,5,5-pentafluoropentyl)-vinyl sulfide in 74 ml of glacial acetic acid is mixed drop by drop with 59 ml of 30% hydrogen peroxide in such a way that the reaction temperature does not exceed 70° C. Then, it is stirred for one hour at a bath temperature of 70° C. Then, it is added to water, extracted three times with ethyl acetate, washed with sodium thiosulfate, water and common salt solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 12.3 g of (4,4,5,5,5-pentafluoropentyl)-vinyl sulfone is obtained as an oil.

Workup

  1. customdoes not exceed 70° C
  2. extractionextracted three times with ethyl acetate
  3. washwashed with sodium thiosulfate, water and common salt solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-54f3510bdd884f0bba5d72f95ce97525
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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