Potassium Hydroxide → 2'-(Carboxymethoxy)-4'-(3-methyl-2-butenyloxy)-4-(2-propenyl)chalcone

HRID 1534692Notes

Reaction equation

HRID 1534692 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH:9]=[CH:8][C:7]=1[C:18](=[O:20])[CH3:19])([OH:3])=[O:2].[CH2:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[CH:22]=[CH2:23].[OH-].[K+]>C(O)C>[C:1]([CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([CH3:16])[CH3:17])[CH:9]=[CH:8][C:7]=1[C:18](=[O:20])[CH:19]=[CH:28][C:27]1[CH:30]=[CH:31][C:24]([CH2:21][CH:22]=[CH2:23])=[CH:25][CH:26]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 13247580{2-Acetyl-5-[(3-methylbut-2-en-1-yl)oxy]phenoxy}acetic acidHCID 132917624-(Prop-2-en-1-yl)benzaldehyde

Product 1

HCID 541478252'-(Carboxymethoxy)-4'-(3-methyl-2-butenyloxy)-4-(2-propenyl)chalconeYield 29.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 834 mg of 2'-(1-carboxymethoxy)-4'-(3-methyl-2-butenyloxy)acetophenone and 500 mg of 4-(2-propenyl)benzaldehyde in 10 ml of ethanol was added 842 mg of potassium hydroxide, and the mixture was stirred for 20 minutes. After neutralization with dilute hydrochloric acid, the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate - n-hexane to give 360 mg of the title compound as a pale yellow needles.

Workup

  1. extractionAfter neutralization with dilute hydrochloric acid, the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate - n-hexane

Sources & evidence

ORD record
ord-fd288b1651bc4900b0bcbd1cefc78b8d
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

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