Water ethanol → HCID 87700615, compound

HRID 985372Notes

Reaction equation

HRID 985372 reaction equation
[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][O:5][C:6](=[O:23])/[C:7](/[CH2:12][C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[CH:8]\[C:9]([O-:11])=[O:10])[CH3:2].[S:28]([O-:31])([OH:30])=[O:29].[Na+:32].O.C(O)C>C(OCC)(=O)C>[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][O:5][C:6](=[O:23])[C:7]([CH2:12][C:13]([F:21])([F:22])[C:14]([F:19])([F:20])[C:15]([F:17])([F:18])[F:16])([S:28]([OH:31])(=[O:30])=[O:29])[CH2:8][C:9]([O-:11])=[O:10])[CH3:2].[Na+:32]

Participants

5

Reactant 3

HCID 19096565Water ethanolHCID 23665763Sodium BisulfiteHCID 131724801HCID 131724801, compound

Product 1

HCID 87700615HCID 87700615, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Mono(2-ethylhexyl)mono(2,2,3,3,4,4,4-heptafluorobutyl)maleate (80.3 g, 0.196 mol), sodium hydrogensulfite (20.4 g, 0.196 mol) and water/ethanol (80 mL, 1:1 (v/v)) were mixed and refluxed for 10 hours with heating. Then, the reaction mixture was added with ethyl acetate (1000 mL), and the organic phase was washed with saturated sodium chloride aqueous solution. Thereafter, the organic layer was collected, and the organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1 (v/v)). The corrected organic phase was washed with a saturated sodium chloride aqueous solution, and then the organic solvent was evaporated under reduced pressure to obtain the target compound (32 g, yield: 32%) as colorless transparent solid.

Workup

  1. temperaturerefluxed for 10 hours
  2. temperaturewith heating
  3. washthe organic phase was washed with saturated sodium chloride aqueous solution
  4. customThereafter, the organic layer was collected
  5. customthe organic solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=9/1 (v/v))
  7. washThe corrected organic phase was washed with a saturated sodium chloride aqueous solution
  8. customthe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-786880b1bd7246508a4aacb5a8d33c6b
Source dataset
uspto-grants-2005_03
Patent number
US06872515B2

Reaction notes

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