Iodoacetic Acid → 2-benzoylsulfanylacetic Acid

HRID 1900212Notes

Reaction equation

HRID 1900212 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 (7.98 g, 99% yield) benzoylmercaptoacetic acid.

Workup

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

Sources & evidence

ORD record
ord-6ffaf6a343fb408398eb21be0dd3cf84
Source dataset
uspto-grants-1996_11
Patent number
US05574140

Reaction notes

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