Iodoacetic Acid → 2-benzoylsulfanylacetic Acid

HRID 481737Notes

Reaction equation

HRID 481737 reaction equation
[C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].I[CH2:13][C:14]([OH:16])=[O:15]>C(O)C.O>[C:1]([S:8][CH2:13][C:14]([OH:16])=[O:15])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5240Iodoacetic AcidHCID 14797Potassium HydroxideHCID 178526132HCID 178526132, compound

Product 1

HCID 51165332-benzoylsulfanylacetic AcidYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

To a purged stirring solution at 0° C. of (5.74 g, 41.6 mmoles) thiobenzoic acid in (100 mL) ethanol was added (27.8 mL, 3N, 83.2 mmoles) potassium hydroxide followed by (7.70 g, 41.6 mmoles) iodoacetic acid in (30 mL) ethanol. The solution stirred for 10 hours at room temperature under argon. The ethanol was rotavapped and the orange solid product was dissolved in (40 mL) water. The solution was acidified to pH 2.0 where an orange precipitate formed. This was filtered, washed with water, and dried in vacuo to give an orange-pink solid, benzoylmercaptoacetic acid (7.98 g, 99% yield).

Workup

  1. customformed
  2. filtrationThis was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-73129ab070a44633a1f807d7c34badf6
Source dataset
uspto-grants-1998_08
Patent number
US05789555

Reaction notes

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