Water ethanol → HCID 23721976, compound

HRID 985373Notes

Reaction equation

HRID 985373 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

Monodecyl mono(3,3,4,4,5,5,6,6,6-nonafluorohexyl)maleate (48.0 g, 90 mmol), sodium hydrogensulfite (10.4 g, 99 mmol) and water/ethanol (50 mL, 1/1 (v/v)) were mixed and refluxed for 5 hours with heating. Then, the reaction mixture was added with ethyl acetate, 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 recrystallized from acetonitrile to obtain the target compound (12.5 g, yield: 22%) as colorless transparent solid.

Workup

  1. temperaturerefluxed for 5 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 recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b08bc3ca82a44533b5142502e1f08e25
Source dataset
uspto-grants-2005_03
Patent number
US06872515B2

Reaction notes

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