Sodium Hydroxide → 2-(2-Fluorophenyl)-2-methylpropanoic acid

HRID 471215Notes

Reaction equation

HRID 471215 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=[O:12]>O.CO.C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([CH3:16])([CH3:15])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57421199Methyl 2-(2-fluorophenyl)-2-methylpropanoate

Product 1

HCID 259167252-(2-Fluorophenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of sodium hydroxide (1 g) in water (50 mL) was added to a solution of methyl 2-(2-fluorophenyl)-2-methylpropanoate (example 90, step b) (2.6 g) in methanol (50 mL) and THF (50 mL). The reaction mixture was heated at 40° C. for 40 hours. The organics were removed under reduced pressure and the remaining aqueous solution washed with ethyl acetate. The aqueous layer was cooled and acidified by addition of concentrated HCl. The mixture was extracted with ethyl acetate and the organic layer washed with brine before being dried over sodium sulphate, filtered and the solvent removed under reduced pressure to afford the subtitled compound. Yield 1.5 g.

Workup

  1. customThe organics were removed under reduced pressure
  2. washthe remaining aqueous solution washed with ethyl acetate
  3. temperatureThe aqueous layer was cooled
  4. additionacidified by addition of concentrated HCl
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer washed with brine
  7. dry with materialbefore being dried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7695df5073eb4b428452165c51ab01a3
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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