Water ethanol → HCID 87700736, compound

HRID 985374Notes

Reaction equation

HRID 985374 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

Mono(2-ethylhexyl)mono(3,3,4,4,5,5,6,6,6-nonafluorohexyl)maleate (137.5 g, 0.29 mol), sodium hydrogensulfite (33.2 g, 0.32 mol) and water/ethanol (140 mL, 1/1 (v/v)) were mixed and refluxed for 2 hours with heating. Thereafter, the reaction mixture was added with ethyl acetate (1000 mL), and the organic phase was washed with a saturated sodium chloride aqueous solution. The organic layer was collected, and the organic solvent was evaporated under reduced pressure. The residue was subjected to recrystallization from toluene (800 mL). Upon cooling on an ice bath, crystals deposited. The crystals were finally separated by filtration to obtain the target compound (140 g, yield: 84%), which was colorless and transparent.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturewith heating
  3. washthe organic phase was washed with a saturated sodium chloride aqueous solution
  4. customThe organic layer was collected
  5. customthe organic solvent was evaporated under reduced pressure
  6. customThe residue was subjected to recrystallization from toluene (800 mL)
  7. temperatureUpon cooling on an ice bath
  8. customThe crystals were finally separated by filtration

Sources & evidence

ORD record
ord-0397636417bb454eabd44df571823e37
Source dataset
uspto-grants-2005_03
Patent number
US06872515B2

Reaction notes

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