Ethanol → 2-(2-Fluorophenyl)-2-methylpropanoic acid

HRID 1868696Notes

Reaction equation

HRID 1868696 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10].[OH-].[K+].CCO>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 57421199Methyl 2-(2-fluorophenyl)-2-methylpropanoate

Product 1

HCID 259167252-(2-Fluorophenyl)-2-methylpropanoic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

A flask containing a solution of methyl 2-(2-fluorophenyl)-2-methylpropanoate (5.2 g, 27 mmol), KOH (2.9 mL, 106 mmol), water (20.0 mL), and EtOH (100 mL) was sealed and heated at 130° C. for 2 hours. Removal of solvent in vacuo provided a yellow oil that was diluted with water. The aqueous mixture was extracted with DCM (1×100 mL), and the organic layer was separated. The aqueous layer was acidified to a pH of 1 with 5N HCl and then extracted with EtOAc (2×100 mL). The organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to afford 4 g of the product as a solid. MS (m/z)=181 (M−1)−.

Workup

  1. customwas sealed
  2. customRemoval of solvent in vacuo
  3. customprovided a yellow oil that
  4. extractionThe aqueous mixture was extracted with DCM (1×100 mL)
  5. customthe organic layer was separated
  6. extractionextracted with EtOAc (2×100 mL)
  7. dry with materialThe organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac6cb7977342438ebc576b3370084ace
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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