Lithium Hydroxide → 2-(2-Fluoro-phenyl)-propionic acid

HRID 1600836Notes

Reaction equation

HRID 1600836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:13])[C:9]([O:11]C)=[O:10].[Li+].[OH-]>C1COCC1.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:13])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 21830852Methyl 2-(2-fluorophenyl)propanoate

Product 1

HCID 184215882-(2-Fluoro-phenyl)-propionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-fluorophenyl)propanoate (26.2 g, 0.144 mol) was dissolved in THF (325 ml) and LiOH (1 M, 173 ml) added. The reaction mixture was stirred at room temperature for 2.5 h, before diluting with diethyl ether and extracting with water and 1N NaOH. The aqueous layer was acidified and extracted with ethyl acetate (×2). The organic extract was washed with brine, dried and evaporated to yield 2-(2-fluorophenyl)propanoic acid (22.5 g, 100%) as an oil.

Workup

  1. extractionextracting with water and 1N NaOH
  2. extractionextracted with ethyl acetate (×2)
  3. extractionThe organic extract
  4. washwas washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ca3c10a8dc634bacbb693a6f4653d07f
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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