Sodium Hydroxide → HCID 57804135, compound

HRID 2102898Notes

Reaction equation

HRID 2102898 reaction equation
[F:1][C:2]([F:17])([F:16])/[C:3](/[CH3:15])=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=1.[OH-].[Na+]>C1COCC1.CO>[F:1][C:2]([F:16])([F:17])/[C:3](/[CH3:15])=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57804162HCID 57804162, compound

Product 1

HCID 57804135HCID 57804135, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of methyl (E)-4-(3,3,3-trifluoro-2-methylprop-1-enyl)benzoate (60 mg, 0.25 mmol) in THF (5 mL) and MeOH (5 mL) was added a 2N NaOH solution (1 mL). The mixture was stirred at room temperature for 10 h. After removal of the organic solvent in vacuo, the mixture was treated with water and acidified with 1N HCl to pH 2-3. The mixture was extracted with EtOAc (20 mL×3). The combined extracts were washed with brine, dried (Na2SO4), and evaporated. The residue was purified with column to give (E)-4-(3,3,3-trifluoro-2-methylprop-1-enyl)benzoic acid as a white solid. LC-MS: tR=3.04 min, m/z=229 (M−1).

Workup

  1. customAfter removal of the organic solvent in vacuo
  2. additionthe mixture was treated with water
  3. extractionThe mixture was extracted with EtOAc (20 mL×3)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified with column

Sources & evidence

ORD record
ord-bf18265ccd7e4ce38f22c28ef6918e6e
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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