Sodium Hydroxide → 3-(3-Fluoro-4-methoxyphenyl)propionic acid

HRID 2378531Notes

Reaction equation

HRID 2378531 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22558762HCID 22558762, compound

Product 1

HCID 30179663-(3-Fluoro-4-methoxyphenyl)propionic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Intermediate 8 (2.97 g) in methanol (40.0 ml) was added with 2 N aqueous sodium hydroxide (15.0 ml) and stirred at 60° C. for 16 hours. The reaction mixture was concentrated under reduced pressure, then made acidic with aqueous 5% hydrochloric acid under ice cooling, and extracted with ethyl acetate (200 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 9, 2.40 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate (200 ml)
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-68de19d5683944119957a4a47c781761
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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