Isoprene → HCID 12905479, compound

HRID 1659809Notes

Reaction equation

HRID 1659809 reaction equation
[F:1][C:2]([F:16])([S:13]([OH:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[CH2:17]=[CH:18][C:19](=[CH2:21])[CH3:20].C([O-])(O)=O.[Na+]>>[CH3:20][C:19]([CH3:21])=[CH:18][CH2:17][S:13]([C:2]([F:1])([F:16])[C:3]([F:11])([F:12])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6])(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 6557IsopreneHCID 516892Sodium BicarbonateHCID 596595Perfluorobutane-1-sulfinic acid

Product 1

HCID 12905479HCID 12905479, compoundYield 60%

Conditions

Temperature
0 °C

Procedure

25 g (0.088 mol) of perfluorobutanesulphinic acid were initially introduced into a 100 ml three-necked flask and cooled to 0° C. Freshly distilled isoprene was then added dropwise, in excess, during which a dropping rate of 1 drop per minute had to be maintained. After the dropwise addition, the solution was immediately poured into ice-water neutralized with NaHCO3 and extracted with ether. After drying with MgSO4, the ether extract was filtered, the ether was stripped off from the filtrate in a rotary evaporator and the residue was distilled. Perfluorobutyl 3-methyl-2-butenyl sulphone of boiling point 41° C./0.1 mm Hg was obtained as a yellowish-tinged liquid in a yield of 60 to 70% of theory.

Workup

  1. temperatureto be maintained
  2. additionAfter the dropwise addition
  3. extractionextracted with ether
  4. dry with materialAfter drying with MgSO4
  5. extractionthe ether extract
  6. filtrationwas filtered
  7. customthe ether was stripped off from the filtrate in a rotary evaporator
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-9ae0c2a2b46c4e0a8867a37c8512a1c3
Source dataset
uspto-grants-1981_12
Patent number
US04305885

Reaction notes

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