Sodium Hydroxide → 3-(2-Fluorophenyl)propanoic acid

HRID 362829Notes

Reaction equation

HRID 362829 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12]CC)=[O:11].[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14879014Ethyl 3-(2-fluorophenyl)propanoate

Product 1

HCID 20638663-(2-Fluorophenyl)propanoic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(2-fluorophenyl)propionate (25.54 g, 0.130 mol) and a 50% aqueous solution of sodium hydroxide (30 mL) in water (130 mL) was refluxed for 2 h. After cooling the mixture was washed with diethyl ether (2×100 mL). The aqueous phase was chilled in an ice bath, and the pH was adjusted to 3 with hydrochloric acid . The white precipitate which formed was collected by filtration, washed repeatedly with water, and dried in a vacuum at 60° C. for 18 h to give 18.66 g (85%) of 3-(2-fluorophenyl)propionic acid as a white solid; m.p., 72°-74° C. This material was used without further purification.

Workup

  1. temperatureAfter cooling the mixture
  2. washwas washed with diethyl ether (2×100 mL)
  3. temperatureThe aqueous phase was chilled in an ice bath
  4. customThe white precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed repeatedly with water
  7. customdried in a vacuum at 60° C. for 18 h

Sources & evidence

ORD record
ord-e32e5ff2b6084dcab673d88d7df6f0ba
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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