Ethyl 4,4,4-trifluoro-2-methylbut-2-enoic acid → 4,4,4-Trifluoro-2-methylbut-2-enoic acid

HRID 20447Notes

Reaction equation

HRID 20447 reaction equation
C([C:3]([C:9]([F:12])([F:11])[F:10])=[C:4]([CH3:8])[C:5]([OH:7])=[O:6])C>S(=O)(=O)(O)O>[F:10][C:9]([F:12])([F:11])[CH:3]=[C:4]([CH3:8])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 53430161Ethyl 4,4,4-trifluoro-2-methylbut-2-enoic acid

Product 1

HCID 534060794,4,4-Trifluoro-2-methylbut-2-enoic acidYield 62.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Heat a solution of ethyl 4,4,4-trifluoro-2-methylbut-2-enoic acid (0.544 g, 2.99 mmol) in 5M sulfuric acid (5 mL) at 120° C. for 2.5 days. Saturate the solution with sodium chloride and extract with diethyl ether (1×40 mL). Dry the organic phase with magnesium sulfate and concentrate under reduced pressure to provide 0.288 g (62.6%) of the title compound.

Workup

  1. concentrationSaturate the solution with sodium chloride
  2. extractionextract with diethyl ether (1×40 mL)
  3. dry with materialDry the organic phase with magnesium sulfate
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-3ccbdfc005e14e1288f33b802a9d1578
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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