HCID 14724207, compound → HCID 15595233, compound

HRID 1906318Notes

Reaction equation

HRID 1906318 reaction equation
[C:1]([O:5][C:6]([C:8]([CH:18](F)[F:19])([CH2:14][CH:15]([CH3:17])[CH3:16])C(OCC)=O)=[O:7])(C)(C)[CH3:2]>FC(F)(F)C(O)=O>[CH2:14](/[C:8](=[CH:18]\[F:19])/[C:6]([O:5][CH2:1][CH3:2])=[O:7])[CH:15]([CH3:16])[CH3:17]

Participants

3

Reactant 1

HCID 14724207HCID 14724207, compound

Product 1

HCID 15595233HCID 15595233, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 2-(tert-butoxycarbonyl)-2-(difluoromethyl)-4-methylvalerate (35.68 g) in trifluoroacetic acid (243 ml) is stirred for 1 hour, then the excess trifluoroacetic acid is removed by evaporation. The residual oil (30.89 g) is dissolved in THF (400 ml) and treated slowly with M NaOH (121 ml) so that the pH does not rise above 7.02. After completion of the addition the solution is stirred for another 15 minutes and the product is extracted into ether. Careful distillation at atmospheric pressure, then at 24mm allows the separation of essentially pure acrylate as a colorless oil (5.72 g), bp 70°-72° C.

Workup

  1. customthe excess trifluoroacetic acid is removed by evaporation
  2. dissolutionThe residual oil (30.89 g) is dissolved in THF (400 ml)
  3. additiontreated slowly with M NaOH (121 ml) so that the pH
  4. additionAfter completion of the addition the solution
  5. extractionthe product is extracted into ether
  6. distillationCareful distillation at atmospheric pressure
  7. customthe separation of essentially pure acrylate as a colorless oil (5.72 g), bp 70°-72° C.

Sources & evidence

ORD record
ord-aad31c2162dc47fc87ecc2df350afec7
Source dataset
uspto-grants-1987_03
Patent number
US04650907

Reaction notes

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