Hydrochloric Acid → 70329-37-2

HRID 1242804Notes

Reaction equation

HRID 1242804 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[CH2:8]([C:10]1[S:14][C:13](C=O)=[CH:12][CH:11]=1)[CH3:9].N1CCCCC1.Cl>N1C=CC=CC=1.O>[CH2:8]([C:10]1[S:14][C:13](/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1)[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 1698305-Ethyl-2-thiophenecarboxaldehyde

Product 1

HCID 78791970329-37-2Yield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of malonic acid (5.9 g) and 5-ethyl-2-thiophenecarboxaldehyde (4.0 g) in dry pyridine (12 mL) was added piperidine (0.42 mL). The reaction mixture was stirred at 80° C. for 17 hours, chilled and diluted with water (70 mL). This mixture was acidified with concentrated HCl (14 mL) and the white precipitate was collected by filtration, washed with water (5×10 mL) and dried under vacuum giving (2E)-3-(5-ethyl(2-thienyl))prop-2-enoic acid (5.0 g). Yield=96%

Workup

  1. temperaturechilled
  2. filtrationthe white precipitate was collected by filtration
  3. washwashed with water (5×10 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1fa9ca23f2e64feda52aa64d90e6a403
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

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