Water ethanol → HCID 23721976, compound

HRID 2212801Notes

Reaction equation

HRID 2212801 reaction equation
[F:1][C:2]([F:33])([C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[CH2:3][CH2:4]/[C:5](=[CH:19]/[C:20]([O-:22])=[O:21])/[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:7].[S:34]([O-:37])([OH:36])=[O:35].[Na+:38].O.C(O)C>C(OCC)(=O)C>[F:1][C:2]([F:33])([C:23]([F:31])([F:32])[C:24]([F:29])([F:30])[C:25]([F:28])([F:27])[F:26])[CH2:3][CH2:4][C:5]([S:34]([OH:37])(=[O:36])=[O:35])([CH2:19][C:20]([O-:22])=[O:21])[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:7].[Na+:38]

Participants

5

Reactant 3

HCID 19096565Water ethanolHCID 23665763Sodium BisulfiteHCID 86759623HCID 86759623, compound

Product 1

HCID 23721976HCID 23721976, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

48.0 g (90 mmol) of monodecyl mono(3,3,4,4,5,5,6,6,6-nonafluorohexyl)maleate, 10.4 g (99 mmol) of sodium hydrogen sulfite and 50 mL of water/ethanol (1/1 v/v) were mixed together and heated under reflux for 5 hr. Thereafter, 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 acetonitrile was performed, thereby obtaining 12.5 g (yield: 22%) of desired compound as a colorless transparent solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 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 acetonitrile

Sources & evidence

ORD record
ord-3a29bbfc86d742b4921d89058f39b86d
Source dataset
uspto-grants-2006_09
Patent number
US07105285B2

Reaction notes

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