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

HRID 1290677
Notes
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Reaction equation

HRID 1290677 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 vacua. 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.

Workup

  1. customto yield a viscous liquid which
  2. customwas decanted from the unreacted zinc
  3. customMost of the dioxane was evaporated in vacua
  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-ff34085e6a7a40478a7b6a78e773956c
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753642

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes