Hydrochloric Acid → 3-Thiophen-2-ylprop-2-enoic acid

HRID 880426Notes

Reaction equation

HRID 880426 reaction equation
N1CCCCC1.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=O.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].Cl>N1C=CC=CC=1>[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=[CH:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 73642-ThiophenecarboxaldehydeHCID 8082Piperidine

Product 1

HCID 928683-Thiophen-2-ylprop-2-enoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Piperidine (2.45 g, 0.056 mol) was added drop wise over a period of 10 min to a stirred solution of thiophene-2-carbaldehyde (4.00 g, 0.036 mol) and malonic acid (1.00 g, 0.18 mol) in pyridine (40 mL) at 0° C. and the resulting reaction mixture was refluxed for 2 h. The reaction mixture was poured into 2N HCl (100 mL) and the precipitated solid filtered. The aqueous layer was extracted with ethyl acetate and the organic layer was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 3-(2-thienyl)prop-2-enoic acid (5.00 g, 92%) as a solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 2 h
  3. filtrationthe precipitated solid filtered
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe organic layer was washed with brine solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7439426e1a5f4de28d5b7ab4c0ec57f5
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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