Propionyl chloride → 2',4,4'-Trimethoxy-6'-(propionyloxy)chalcone

HRID 364658

Reaction equation

HRID 364658 reaction equation
[OH:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>N1C=CC=CC=1>[CH3:23][O:22][C:16]1[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:2]([O:1][C:24](=[O:27])[CH2:25][CH3:26])[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 235736Flavokavain A

Product 1

HCID 541174992',4,4'-Trimethoxy-6'-(propionyloxy)chalconeYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 500 mg of 2'-hydroxy-4,4',6'-trimethoxychalcone and 0.15 ml of propionyl chloride in 5 ml of pyridine was stirred at room temperature for 6 hours. After removal of the solvent, the residue was treated with 10 ml of ice-water and 30 ml of chloroform. The mixture was shaken, and the chloroform layer was separated, washed with three 10 ml portions of water, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The oily residue was washed with a small amount of hexane, and the resulting solid was crystallized from ethanol/hexane, yielding 530 mg (90% yield) of 2',4,4'-trimethoxy-6'-(propionyloxy)chalcone as pale yellow needles; m.p. 117°-118° C.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was treated with 10 ml of ice-water and 30 ml of chloroform
  3. customthe chloroform layer was separated
  4. washwashed with three 10 ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. washThe oily residue was washed with a small amount of hexane
  8. customthe resulting solid was crystallized from ethanol/hexane

Sources & evidence

ORD record
ord-f460867658d84ece8432a974c9b8d1bf
Source dataset
uspto-grants-1986_08
Patent number
US04605674

Linked notes

Loading…