Water → HCID 20446202, compound

HRID 2418344Notes

Reaction equation

HRID 2418344 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19]CC)=[O:18].[OH-].[Na+].O>O1CCOCC1>[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20446222HCID 20446222, compound

Product 1

HCID 20446202HCID 20446202, compoundYield 136%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2-[2-amino-3-(2-fluorophenoxy)phenyl]acetate (5.7 g.), sodium hydroxide (1.6 g.), water (25 ml.) and dioxane (25 ml.) was refluxed under heating for 16 hours with stirring. The reaction mixture was left to cool at ambient temperature and dioxane was distilled off under reduced pressure. To the residue was added water and the mixture was washed with diethyl ether. Diethyl ether was added to the aqueous layer and the mixture was adjusted to pH 3 to 4 with 5% sulfuric acid. The diethyl ether layer was separated, washed with water and dried over magnesium sulfate and then the solvent was distilled off under reduced pressure to give 2-[2-amino-3-(2-fluorophenoxy)phenyl]acetic acid (7 g.). This crude substance was recrystallized from a mixture of ethyl acetate and n-hexane to give the pure compound (3.6 g.), mp 122° to 123° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 16 hours
  3. waitThe reaction mixture was left
  4. distillationdioxane was distilled off under reduced pressure
  5. additionTo the residue was added water
  6. washthe mixture was washed with diethyl ether
  7. additionDiethyl ether was added to the aqueous layer
  8. customThe diethyl ether layer was separated
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a6a25be674394bfe98a03827d02da042
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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