Hydrochloric Acid → 2-Benzyl-3-mercaptopropanoic acid

HRID 1646312Notes

Reaction equation

HRID 1646312 reaction equation
C([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8])(=O)C.[OH-].[Na+].Cl>CO>[SH:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic Acid

Product 1

HCID 1943272-Benzyl-3-mercaptopropanoic acidYield 52.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Acetylthiomethyl-3-phenylpropionic acid (18.5 g) is mixed with 70% aqueous methanol (100 ml), and the mixture is stirred at room temperature for one hour under nitrogen while maintaining at pH 13.0 with 20% aqueous sodium hydroxide solution, and thereafter the mixture is adjusted to pH 2.0 with 20% hydrochloric acid, and methanol is distilled off under reduced pressure. The residue is purified by a column chromatography using Diaion HP-20 (eluant, water-acetonitrile). The fractions containing the desired compound are collected and acetonitrile is distilled off under reduced pressure. The aqueous solution is extracted with ethyl acetate. The extract is dried over anhydrous magnesium sulfate, and ethyl acetate is distilled off under reduced pressure to give 2-mercaptomethyl-3-phenylpropionic acid (8 g) as a colorless oily substance.

Workup

  1. distillationis distilled off under reduced pressure
  2. customThe residue is purified by a column chromatography
  3. additionThe fractions containing the desired compound
  4. customare collected
  5. distillationacetonitrile is distilled off under reduced pressure
  6. extractionThe aqueous solution is extracted with ethyl acetate
  7. dry with materialThe extract is dried over anhydrous magnesium sulfate, and ethyl acetate
  8. distillationis distilled off under reduced pressure

Sources & evidence

ORD record
ord-185fb4a7d226420a8a3211cc17c140c1
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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