alpha-Phenylthio-2-thiopheneacetic acid → 2-Thiopheneacetic acid

HRID 27595

Reaction equation

HRID 27595 reaction equation
C1(S[CH:8]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:9]([OH:11])=[O:10])C=CC=CC=1>C(O)(=O)C.[Zn]>[S:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 23460397alpha-Phenylthio-2-thiopheneacetic acid

Product 1

HCID 159702-Thiopheneacetic acidYield 85%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

α-Phenylthio-2-thiopheneacetic acid (890 mg, 3.56 mmol) was dissolved in acetic acid (6 ml), then zinc dust (350 mg, 5.4 mmol) was added and the mixture was heated under reflux with vigorous stirring. After 30 min., zinc dust (350 mg, 5.4 mmol) was added again, and the mixture was heated under reflux for another 4 hr. with stirring, then cooled to room temperature, and most of the solvent was removed by distillation. Water and ethyl acetate were added and the precipitate was filtered off by the use of celite, and the layers of the filtrate were separated. The organic layer was washed with an aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After filtration, the solution was concentrated under a reduced pressure and the crystals thus obtained were further recrystallized from ethyl acetate: n-hexane to give 2-thiopheneacetic acid (430 mg) melting at 62° C. (literature value: 62°-65° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux with vigorous stirring
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for another 4 hr
  5. custommost of the solvent was removed by distillation
  6. additionWater and ethyl acetate were added
  7. filtrationthe precipitate was filtered off by the use of celite
  8. customthe layers of the filtrate were separated
  9. washThe organic layer was washed with an aqueous solution of sodium chloride
  10. dry with materialdried with anhydrous magnesium sulfate
  11. filtrationAfter filtration
  12. concentrationthe solution was concentrated under a reduced pressure
  13. customthe crystals thus obtained
  14. customwere further recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e87aeb7cbdaa4eca9de86254627b734a
Source dataset
uspto-grants-1980_09
Patent number
US04221915

Linked notes

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