Hydrochloric Acid → Piperic acid

HRID 631938Notes

Reaction equation

HRID 631938 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11](N2CCCCC2)=[O:12])=[CH:5][C:4]2[O:19][CH2:20][O:21][C:3]=2[CH:2]=1.[OH-:22].[K+].Cl>C(O)C>[O:21]1[C:3]2[CH:2]=[CH:1][C:6](/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11]([OH:12])=[O:22])=[CH:5][C:4]=2[O:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 638024Piperine

Product 1

HCID 5370536Piperic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperine (200 mg, 0.70 mmol) dissolved in anhydrous ethanol and KOH (1.18 g, 21.0 mmol) were mixed and heated to reflux for 12 hours. Upon completion of the experiment, the pH value of the reaction mixture solution was adjusted to 2-3 using hydrochloric acid. After the ethanol was distilled under reduced pressure, the residue was diluted with EtOAC (30 mL) and washed with a saturated solution of NaCl, followed by drying over anhydrous Na2SO4. The solvent was distilled under reduced pressure to give a target compound (121 mg, yield: 79.1%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. distillationAfter the ethanol was distilled under reduced pressure
  4. additionthe residue was diluted with EtOAC (30 mL)
  5. washwashed with a saturated solution of NaCl
  6. dry with materialby drying over anhydrous Na2SO4
  7. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-87436eee3392488f87d68225bb8e11aa
Source dataset
uspto-grants-2016_04
Patent number
US09321751B2

Reaction notes

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