Potassium Hydroxide → 4-(2-Carboxy-benzyl-thio)phenyl-acetic acid

HRID 268034Notes

Reaction equation

HRID 268034 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([OH:24])=[O:23])=[CH:10][CH:9]=1)C>O.C(O)C>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][S:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]([OH:25])=[O:5])=[CH:9][CH:10]=1)([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 544601824-(2-Carboxybenzyl-thio)phenyl-acetic acid ethyl ester

Product 1

HCID 123300244-(2-Carboxy-benzyl-thio)phenyl-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4.75 g of potassium hydroxide in 20 cc of water is added to 7 g of 4-(2-carboxybenzyl-thio)phenyl-acetic acid ethyl ester in 50 cc of ethanol, and the mixture is stirred at room temperature for 20 hours. The solution is then concentrated at reduced pressure, the residue is taken up in water and extracted with ether. The aqueous phase is subsequently acidified with 5 N hydrochloric acid and extracted with ethyl acetate. After washing the ethyl acetate extract with water and drying over sodium sulphate, the solvent is removed by distillation, whereby 4-(2-carboxy-benzyl-thio)phenyl-acetic acid is obtained as crystalline residue. M.P. 169° (from ethyl acetate/pentane).

Workup

  1. concentrationThe solution is then concentrated at reduced pressure
  2. extractionextracted with ether
  3. extractionextracted with ethyl acetate
  4. washAfter washing the ethyl acetate
  5. extractionextract with water
  6. dry with materialdrying over sodium sulphate
  7. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-03b993b7bb9c4c13a80069737df663da
Source dataset
uspto-grants-1976_03
Patent number
US03946036

Reaction notes

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