Hydrochloric Acid → Piperic acid

HRID 1244512Notes

Reaction equation

HRID 1244512 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+].CO.Cl>O>[CH2:20]1[O:19][C:4]2[CH:5]=[C:6](/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11]([OH:12])=[O:22])[CH:1]=[CH:2][C:3]=2[O:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 638024Piperine

Product 1

HCID 5370536Piperic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To piperine (1) (2 g, 0.7 mmol, 1 eq), 20% of methanolic KOH (100 ml) was added and refluxed for 2 days. After completion of the hydrolysis, methanol was removed under reduced pressure and a yellow coloured oily solid was obtained. This residue was dissolved in water (50 ml) and acidified with 6N HCl to pH <1 yielding a yellowish precipitate of piperinic acid. Recrystallization from methanol gave yellow needles (0.9 g, 60% yield). m.p. 206°-208° C. (Lit m.p. 217 °-218° C.)1 2.2 Synthesis of Piperlonguminine (RV-A06)

Workup

  1. temperaturerefluxed for 2 days
  2. customwas removed under reduced pressure
  3. customa yellow coloured oily solid was obtained

Sources & evidence

ORD record
ord-30e5bd05d6cd41b1ac869e20da2e1bb4
Source dataset
uspto-grants-2006_10
Patent number
US07122561B2

Reaction notes

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