Hydrochloric Acid → 4-(Thiophen-3-yl)butanoic acid

HRID 1598637Notes

Reaction equation

HRID 1598637 reaction equation
O.NN.[OH-].[K+].O=[C:7]([C:16]1[CH:20]=[CH:19][S:18][CH:17]=1)[CH2:8][CH:9](C(O)=O)[C:10]([OH:12])=[O:11].Cl.[Na+].[Cl-]>C(O)CO>[S:18]1[CH:19]=[CH:20][C:16]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:17]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 6611424[2-Oxo-2-(3-thienyl)ethyl]malonic acid

Product 1

HCID 110411434-(Thiophen-3-yl)butanoic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Hydrazine hydrate (1.3 mL, 1.34 g, 26.8 mmol) was added dropwise to a solution of KOH (3.54 g, 63 mmol) and 2-[2-oxo-2-(3-thienyl) ethyl] malonic acid 8(c) (4.00 g, 17.5 mmol) in ethylene glycol (30 mL). This solution was heated at reflux for 6 hours. After cooling to room temperature, the crude reaction mixture was poured into a mixture of 6N HCl (50 mL) and ice (200 g). This aqueous mixture was saturated with NaCl, then extracted with ether (3×70 mL). The combined organic extracts were dried over Na2SO4 and concentrated, in vacuo, to provide an orange oil (2.61 g) of sufficient purity to be employed in the subsequent reaction without any further purification.

Workup

  1. temperatureThis solution was heated
  2. temperatureat reflux for 6 hours
  3. customthe crude reaction mixture
  4. extractionextracted with ether (3×70 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-ce595b78fe2543f5a844324d6ecb659b
Source dataset
uspto-grants-1998_04
Patent number
US05739141

Reaction notes

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