Hydrochloric Acid → (2-{[4-(Carboxymethyl)phenyl]methyl}phenyl)acetic acid

HRID 648116Notes

Reaction equation

HRID 648116 reaction equation
[C:1]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([OH:20])=[O:19])=O)=[CH:7][CH:6]=1)([OH:3])=[O:2].Cl.O.[OH-].[Na+]>CO>[C:1]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([CH2:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([OH:20])=[O:19])=[CH:7][CH:6]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 14798Sodium HydroxideHCID 12740014HCID 12740014, compound

Product 1

HCID 12740020(2-{[4-(Carboxymethyl)phenyl]methyl}phenyl)acetic acidYield 46.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.8 g of 2-(4-carboxymethylbenzoyl)phenylacetic acid in 15 ml of methanol was added to 9.0 g of zinc amalgam, 17.5 ml of conc. hydrochloric acid and 7.5 ml of water. The mixture was heated under reflux for 5 hours with stirring. After the reaction, the reaction mixture was cooled, and the zinc amalgam was removed by decantation. Water (100 ml) was added, and the mixture was extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride. The ether was distilled off to afford a yellow oily product. Methanol (20 ml) was added to dissolve it. Then, 60 ml of a 10% sodium hydroxide solution was added to the solution, and the solution was heated under reflux for 3 hours with stirring. After the reaction, the reaction mixture was cooled, acidified with conc. hydrochloric acid, and extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The ether was then distilled off. The residue was chromatographed on a silica gel column using a mixture of chloroform and methanol (95:5) as an eluent. A solid was obtained from the eluate. Recrystallization from ether afforded 1.67 g of 2-(4-carboxymethylbenzyl)phenylacetic acid as colorless plate-like crystals having a melting point of 155° to 156° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled
  5. customthe zinc amalgam was removed by decantation
  6. additionWater (100 ml) was added
  7. extractionthe mixture was extracted with ether
  8. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  9. distillationThe ether was distilled off
  10. customto afford a yellow oily product
  11. dissolutionto dissolve it
  12. temperaturethe solution was heated
  13. temperatureunder reflux for 3 hours
  14. stirringwith stirring
  15. customAfter the reaction
  16. temperaturethe reaction mixture was cooled
  17. extractionextracted with ether
  18. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  19. dry with materialdried over anhydrous magnesium sulfate
  20. distillationThe ether was then distilled off
  21. customThe residue was chromatographed on a silica gel column
  22. additiona mixture of chloroform and methanol (95:5) as an eluent
  23. customA solid was obtained from the eluate
  24. customRecrystallization from ether

Sources & evidence

ORD record
ord-aebe7ded2343407ba4800a7d34884898
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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