Hydrochloric Acid → (E)-3-Cyclopentylacrylic acid

HRID 1426631Notes

Reaction equation

HRID 1426631 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].N1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C1(C=O)CCCC1.Cl>N1C=CC=CC=1>[CH:9]1(/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 70106Cyclopentanecarbaldehyde

Product 1

HCID 21518240(E)-3-Cyclopentylacrylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of malonic acid (1.06 g, 10.2 mol) in pyridine (1.25 mL) was added piperidine (0.15 mL) and cyclopentanecarbaldehyde (1.00 g, 10.2 mmol). The mixture was heated to 40° C. for 2 hours, followed by stirring at room temperature for 16 hours. The mixture was then cooled in an ice bath and 2N HCl was added to acidify. The product was extracted with ether. The ether extract was washed with aq. HCl and brine, dried over sodium sulfate, filtered, and the solvent was removed in vacuo to afford the product (1.30 g, 77%), which was used without further purification.

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. extractionThe product was extracted with ether
  3. extractionThe ether extract
  4. washwas washed with aq. HCl and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8243793c92d544f9a6811c901db43abb
Source dataset
uspto-grants-2015_01
Patent number
US08933086B2

Reaction notes

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