Potassium Hydroxide → 2-{4-[(4-Chloroanilino)methyl]phenoxy}propanoic acid

HRID 2058090Notes

Reaction equation

HRID 2058090 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([CH3:19])[C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([CH3:19])[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20329856Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate

Product 1

HCID 203298692-{4-[(4-Chloroanilino)methyl]phenoxy}propanoic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of dried methanol are dissolved 10.0 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate and 1.68 g of potassium hydroxide. The mixture is stirred at room temperature for 5 hours. After concentrating the reaction mixture, water is added to the residue, and the resulting solution is washed with ether. The aqueous layer is acidified with hydrochloric acid and extracted with ether. The extract is washed with water, then dried over magnesium sulfate and thereafter the solvent is distilled off. The resulting crystalline residue is recrystallized from benzene to give 8.0 g of 2-[4-(4-chloroanilinomethyl)phenoxy]propionic acid, mp 148° to 149° C.

Workup

  1. concentrationAfter concentrating the reaction mixture, water
  2. additionis added to the residue
  3. washthe resulting solution is washed with ether
  4. extractionextracted with ether
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent is distilled off
  8. customThe resulting crystalline residue is recrystallized from benzene

Sources & evidence

ORD record
ord-df8b60be244c4ceea3725cbed2c1dc83
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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