Water ethanol → HCID 87700615, compound

HRID 2212800Notes

Reaction equation

HRID 2212800 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

80.3 g (0.196 mol) of mono(2-ethylhexyl)mono(2,2,3,3,4,4,4-heptafluorobutyl)maleate, 20.4 g (0.196 mol) of sodium hydrogen sulfite and 80 mL of water/ethanol (1/1 v/v) were mixed together and heated under reflux for 10 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. Purification by silica gel column chromatography (chloroform/methanol: 9/1 v/v) was performed. The collected organic phase was washed with a saturated aqueous sodium chloride solution, and the organic solvent was distilled off in vacuum, thereby obtaining 32 g (yield: 32%) of desired compound as a colorless transparent solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 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. customPurification by silica gel column chromatography (chloroform/methanol: 9/1 v/v)
  7. washThe collected organic phase was washed with a saturated aqueous sodium chloride solution
  8. distillationthe organic solvent was distilled off in vacuum

Sources & evidence

ORD record
ord-b6e7832aa41e4f239d2506f488242aa1
Source dataset
uspto-grants-2006_09
Patent number
US07105285B2

Reaction notes

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