Sodium Hydroxide → HCID 20446142, compound

HRID 2418346Notes

Reaction equation

HRID 2418346 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[Cl:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19]CC)=[O:18].[OH-].[Na+]>O>[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20446151HCID 20446151, compound

Product 1

HCID 20446142HCID 20446142, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-[2-amino-3-(2-chlorophenoxy)phenyl]acetate (4.3 g.), sodium hydroxide (1.1 g.) and water (50 ml.) was refluxed under heating for 5 hours with stirring. The reaction mixture was left to cool at ambient temperature and washed with diethyl ether. To the aqueous solution was added diethyl ether, and the mixture was adjusted to ph 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. The residue (3.4 g.) was crystallized with a mixture of benzene and n-hexane to give 2[2-amino-3-(2-chlorophenoxy)phenyl]acetic acid (1.9 g.). mp 86° to 90° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 5 hours
  3. waitThe reaction mixture was left
  4. washwashed with diethyl ether
  5. additionTo the aqueous solution was added diethyl ether
  6. customThe diethyl ether layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue (3.4 g.) was crystallized with a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-8dcba983d8a749dba50e3e97152e9543
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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