3,5-Dimethoxybenzaldehyde → 3,5-Dimethoxy-4'-prop-2-enyloxychalcone

HRID 394968Notes

Reaction equation

HRID 394968 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:17]=[C:18]([CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1)[CH:19]=O>>[CH3:25][O:24][C:22]1[CH:21]=[C:18]([CH:19]=[CH:1][C:2]([C:4]2[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[CH2:13])=[CH:6][CH:5]=2)=[O:3])[CH:17]=[C:16]([O:15][CH3:14])[CH:23]=1

Participants

3

Reactant 2

HCID 817473,5-DimethoxybenzaldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanone

Product 1

HCID 541070903,5-Dimethoxy-4'-prop-2-enyloxychalconeYield 99%

Procedure

1.76 g (10 mmol) of 4-allyloxyacetophenone and 1.66 g (10 mmol) of 3,5-dimethoxy-benzaldehyde were dissolved in 10 ml of dry freshly distilled ethanol under an inert atmosphere (argon), and the solution was admixed with 100 mg of sodium hydroxide and left under stirring for 18 h. The reaction mixture was filtered to give 2.96 g (99%) of 3,5-dimethoxy-4′-prop-2-enyloxychalcone which was recrystallized from methanol, m.p. 88.5-90° C.

Workup

  1. dry with materialof dry freshly distilled ethanol under an inert atmosphere (argon)
  2. waitleft
  3. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-df68bd4042b3477889afb99aa226e7ba
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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