2,3-Dimethoxybenzaldehyde → 2,3-Dimethoxy-4'-prop-2-enyloxychalcone

HRID 394970Notes

Reaction equation

HRID 394970 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[CH2:13])=[CH:6][CH:5]=1)=[O:3].[CH3:14][O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O>>[CH3:14][O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[CH:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[CH2:13])=[CH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 665812,3-DimethoxybenzaldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanone

Product 1

HCID 544287262,3-Dimethoxy-4'-prop-2-enyloxychalconeYield 90%

Procedure

1.76 g (10 mmol) of 4-allyloxyacetophenone and 1.66 g (10 mmol) of 2,3-dimethoxy-benzaldehyde were under an inert atmosphere (argon) dissolved in 10 ml of dry freshly distilled ethanol, and 100 mg of sodium hydroxide was added to the solution. The mixture was left under stirring for 23 h and concentrated in vacuo. The crystalline residue was recrystallized from methanol-water to give 2.92 g (90%) of 2,3-dimethoxy-4′-prop-2-enyloxychalcone, m.p. 98-99° C.

Workup

  1. dissolutiondissolved in 10 ml
  2. dry with materialof dry freshly distilled ethanol, and 100 mg of sodium hydroxide
  3. additionwas added to the solution
  4. waitThe mixture was left
  5. concentrationconcentrated in vacuo
  6. customThe crystalline residue was recrystallized from methanol-water

Sources & evidence

ORD record
ord-6465f4fa0e04425780ef81273c9724aa
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

Loading…