Sodium Hydroxide → (E)-4-(3,3,3-Trifluoroprop-1-enyl)-2-methoxybenzoic acid

HRID 2102912Notes

Reaction equation

HRID 2102912 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 68702754(E)-methyl 4-(3,3,3-trifluoroprop-1-enyl)-2-methoxybenzoate

Product 1

HCID 57804194(E)-4-(3,3,3-Trifluoroprop-1-enyl)-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (E)-methyl 4-(3,3,3-trifluoroprop-1-enyl)-2-methoxybenzoate (340 mg, 0.0013 mol), MeOH (20 mL), and 2 N aqueous NaOH solution (1.5 mL) was stirred at 65° C. overnight. The solvents were removed under reduced pressure and the residue was treated with water, acidified with 1N HCl to pH 2-3, and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give the product as a white solid. LC-MS: 2.59 min, 244.8 (M−1).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was treated with water
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-49f90e5dc9d74439a38b5181cb17ea77
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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