Methanol → HCID 89444396, compound

HRID 1771687Notes

Reaction equation

HRID 1771687 reaction equation
[F:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[CH:10][CH:9]=[C:8]([F:19])[C:3]=1[C:4]([O:6]C)=[O:5].CO.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[CH:10][CH:9]=[C:8]([F:19])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 89444158HCID 89444158, compound

Product 1

HCID 89444396HCID 89444396, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2,6-difluoro-3-(3-fluorophenyl)benzoate (1.7 g, 6.4 mmol, 1.0 eq) in mixture of MeOH (20 mL) and THF (20 mL) was added a solution of aqueous NaOH (1M aqueous solution, 20 mL, 20 mmol, 3.1 eq) at room temperature. The reaction mixture was heated to reflux for 30 mins, then cooled and the resulting mixture concentrated in vacuo to remove the organic solvent. The residue was diluted with water and adjusted to pH 5-6, by addition of 1M HCl. The precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (1.4 g, 87%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 mins
  3. temperaturecooled
  4. concentrationthe resulting mixture concentrated in vacuo
  5. customto remove the organic solvent
  6. additionThe residue was diluted with water
  7. additionadjusted to pH 5-6, by addition of 1M HCl
  8. customThe precipitate that formed
  9. filtrationwas collected by filtration
  10. washwashed with water
  11. customdried in vacuo

Sources & evidence

ORD record
ord-37008ace41c04931bab3a9136cab6b72
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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