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2-Chloro-2,3,3-trifluorobutanedioic acid → 2,2,3-Trifluorobutanedioic acid

HRID 2072
Notes
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Reaction equation

HRID 2072 reaction equation
Cl[C:2]([F:12])([C:9]([OH:11])=[O:10])[C:3]([F:8])([F:7])[C:4]([OH:6])=[O:5]>O1CCOCC1.[Zn]>[F:7][C:3]([F:8])([CH:2]([F:12])[C:9]([OH:11])=[O:10])[C:4]([OH:6])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 189170672-Chloro-2,3,3-trifluorobutanedioic acid

Product 1

HCID 190657982,2,3-Trifluorobutanedioic acidYield 40.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The residue was dissolved in 100 ml H2O and a solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added. The solution was extracted with ether (3×100 ml) and dried over anhydrous MgSO4. The organic layer was stripped to yield 8.3 g (32%) of the product as a crystalline solid.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customto yield a viscous liquid which
  2. customwas decanted from the unreacted zinc
  3. customMost of the dioxane was evaporated in vacuo
  4. dissolutionThe residue was dissolved in 100 ml H2O
  5. additiona solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added
  6. extractionThe solution was extracted with ether (3×100 ml)
  7. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-2c3cde5cb45a452d9dc003d173196948
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728694

Reaction notes

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