2,5-Dimethoxybenzaldehyde → 2,5-Dimethoxy-4'-prop-2-enyloxychalcone

HRID 394969Notes

Reaction equation

HRID 394969 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]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=1[CH:18]=O>>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[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 667262,5-DimethoxybenzaldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanone

Product 1

HCID 541484062,5-Dimethoxy-4'-prop-2-enyloxychalconeYield 83%

Procedure

1.76 g (10 mmol) of 4-allyloxyacetophenone and 1.66 g (10 mmol) of 2,5-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 2.5 h and filtered. The precipitate was recrystallized from methanol to give 2.50 g (83%) of 2,5-dimethoxy-4′-prop-2-enyloxychalcone, m.p. 86-87° 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. filtrationfiltered
  6. customThe precipitate was recrystallized from methanol

Sources & evidence

ORD record
ord-c1cd1a4b4781411cbfa4335d7cded9f1
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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