Benzoyl Peroxide → 3-(Acetylthio)butanoic acid

HRID 1391193Notes

Reaction equation

HRID 1391193 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].[C:5]([OH:10])(=[O:9])/[CH:6]=[CH:7]/[CH3:8].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O1CCOCC1>[C:1]([S:3][CH:7]([CH3:8])[CH2:6][C:5]([OH:10])=[O:9])(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 637090Crotonic AcidHCID 178418634HCID 178418634, compound

Product 1

HCID 2577073-(Acetylthio)butanoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

40 ml of thioacetic acid are added to 43 g of crotonic acid in 100 ml of dioxane. After adding 20 mg of benzoyl peroxide, the mixture is kept at the boiling point under reflux for 6 hours. The solvent and the excess thioacetic acid are removed by distillation and the product is purified by vacuum distillation. 75 g (92% of theory) of 3-acetylmercapto-butyric acid are obtained; boiling point 94° to 95° C/0.45 mm Hg. nD20 1.4908.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe solvent and the excess thioacetic acid are removed by distillation
  3. distillationthe product is purified by vacuum distillation

Sources & evidence

ORD record
ord-b3ae3cfc5ec144bbb2b8b1ad3c9b775d
Source dataset
uspto-grants-1979_02
Patent number
US04141734

Reaction notes

Loading…