2,4-Dimethoxybenzaldehyde → 2,4-Dimethoxy-4'-(2-propenyloxy)chalcone

HRID 394965Notes

Reaction equation

HRID 394965 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[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH:18]=O>>[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[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 691752,4-DimethoxybenzaldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanone

Product 1

HCID 545548812,4-Dimethoxy-4'-(2-propenyloxy)chalconeYield 97%

Procedure

17.6 g (0.1 mol) of 4-allyloxyacetophenone and 16.6 g (0.1 mol) of 2,4-dimethoxy-benzaldehyde were under an inert dry atmosphere (argon) dissolved in 100 ml of dry ethanol (freshly distilled from sodium under argon atmosphere). The solution was added 1 g of sodium hydroxide and left under stirring for 18 h. The reaction mixture was filtered to give 29.9 g (97%) of 2,4-dimethoxy-4′-prop-2-enyloxychalcone identical to that obtained in Example 2.22, m.p. 74.5-75° C.

Workup

  1. customan inert dry atmosphere (argon)
  2. dissolutiondissolved in 100 ml of dry ethanol (
  3. distillationfreshly distilled from sodium under argon atmosphere)
  4. additionThe solution was added 1 g of sodium hydroxide
  5. waitleft
  6. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-9e1e8a7f4a29410fb3eeeea0d9614ed9
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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