Sodium Hydroxide → HCID 57804219, compound

HRID 2102913Notes

Reaction equation

HRID 2102913 reaction equation
[F:1][C:2]([F:18])([F:17])/[CH:3]=[CH:4]\[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1.[OH-].[Na+]>CO>[F:1][C:2]([F:17])([F:18])/[CH:3]=[CH:4]\[C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68707157HCID 68707157, compound

Product 1

HCID 57804219HCID 57804219, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (Z)-methyl 4-(3,3,3-trifluoroprop-1-enyl)-2-methoxybenzoate (60.0 mg, 0.000230 mol), MeOH (10 mL), and 2 N aqueous NaOH solution (0.5 mL) was stirred at 65° C. for 5 h. After cooling the mixture, the solvent was removed under reduced pressure. The residue was treated with water, acidified with 1N HCl to pH 2-3, and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give the product as a syrup which became an off-white solid while standing at room temperature for a long time. LC-MS: 2.49 min, 244.8 (M−1).

Workup

  1. temperatureAfter cooling the mixture
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was treated with water
  4. extractionextracted with EtOAc (30 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a13d9a5456a4942b14f1c4921965304
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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