Water ethanol → HCID 87700736, compound

HRID 2212802Notes

Reaction equation

HRID 2212802 reaction equation
[CH2:1]([CH:3]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:4][O:5][C:6](=[O:27])/[C:7](/[CH2:12][CH2:13][C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:8]\[C:9]([O-:11])=[O:10])[CH3:2].[S:32]([O-:35])([OH:34])=[O:33].[Na+:36].O.C(O)C>C(OCC)(=O)C>[CH2:1]([CH:3]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:4][O:5][C:6](=[O:27])[C:7]([CH2:12][CH2:13][C:14]([F:25])([F:26])[C:15]([F:23])([F:24])[C:16]([F:21])([F:22])[C:17]([F:19])([F:20])[F:18])([S:32]([OH:35])(=[O:34])=[O:33])[CH2:8][C:9]([O-:11])=[O:10])[CH3:2].[Na+:36]

Participants

5

Reactant 3

HCID 19096565Water ethanolHCID 23665763Sodium BisulfiteHCID 131724802HCID 131724802, compound

Product 1

HCID 87700736HCID 87700736, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

137.5 g (0.29 mol) of mono(2-ethylhexyl)mono(3,3,4,4,5,5,6,6,6-nonafluorohexyl)maleate, 33.2 g (0.32 mol) of sodium hydrogen sulfite and 140 mL of water/ethanol (1/1 v/v) were mixed together and heated under reflux for 2 hr. Thereafter, 1000 mL of ethyl acetate was added, and the organic phase was washed with a saturated aqueous sodium chloride solution. The resultant organic layer was collected, and the organic solvent was distilled off in vacuum. Recrystallization from 800 mL of toluene was performed. Crystal was precipitated by cooling with an ice bath, and finally collected by filtration. As a result, there was obtained 140 g (yield: 84%) of colorless transparent desired compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. washthe organic phase was washed with a saturated aqueous sodium chloride solution
  4. customThe resultant organic layer was collected
  5. distillationthe organic solvent was distilled off in vacuum
  6. customRecrystallization from 800 mL of toluene
  7. customCrystal was precipitated
  8. temperatureby cooling with an ice bath
  9. filtrationfinally collected by filtration

Sources & evidence

ORD record
ord-1a426a7107394f0eb0a8a1e40bed6e2a
Source dataset
uspto-grants-2006_09
Patent number
US07105285B2

Reaction notes

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