Hydrochloric Acid → 2-(Thiophen-2-yl)propanoic acid

HRID 1660470Notes

Reaction equation

HRID 1660470 reaction equation
Cl.CS[C:4]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)([CH3:8])[C:5]([OH:7])=[O:6]>[Zn].O>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH:4]([CH3:8])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12917678HCID 12917678, compound

Product 1

HCID 30169222-(Thiophen-2-yl)propanoic acidYield 58.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Zinc powder (150 mg), 2 ml of conc. hydrochloric acid and 1 ml of water were added to 542 mg of α-methylthio-α-(2-thienyl)propionic acid, and the mixture was stirred at the refluxing temperature for 40 minutes. After cooling, it was extracted three times with 10 ml of diethyl ether. The organic layer was washed twice with 10 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to short-path distillation (bath temperature 140°-160° C./12 mmHg) to afford 245 mg of α-(2-thienyl)propionic acid in a yield of 58%.

Workup

  1. temperatureAfter cooling
  2. extractionit was extracted three times with 10 ml of diethyl ether
  3. washThe organic layer was washed twice with 10 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. distillationthe residue was subjected to short-path distillation (bath temperature 140°-160° C./12 mmHg)

Sources & evidence

ORD record
ord-6312df566dfc4d2c870e70758ddd4f15
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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