Veratraldehyde → 3,4-Dimethoxy-4'-allyloxychalcone

HRID 394966Notes

Reaction equation

HRID 394966 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]=[CH:22][C:23]=1[O:24][CH3:25])[CH:19]=O>C(O)C>[CH3:14][O:15][C:16]1[CH:17]=[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:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 8419VeratraldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanone

Product 1

HCID 544817843,4-Dimethoxy-4'-allyloxychalconeYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.76 g (10 mmol) of 4-allyloxyacetophenone and 1.66 g (10 mmol) of 3,4-dimethoxy-benzaldehyde were under a dry inert atmosphere (argon) dissolved in 10 ml dry ethanol and the solution was stirred for 18 h. The solution was filtered to give 3.0 g (99%) of 3,4-dimethoxy-4′-prop-2-enyloxychalcone which was recrystallized from ethanol, m.p. 74.5-75° C.

Workup

  1. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-dbf5cc4446424f9ab9dc0b2599a80df7
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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