Acetone → 4-(3,4-Dimethoxyphenyl)but-3-en-2-one

HRID 38670Notes

Reaction equation

HRID 38670 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.O.[OH-].[Na+].Cl.[CH3:17][C:18]([CH3:20])=[O:19]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:17][C:18](=[O:19])[CH3:20])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

7

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 8419VeratraldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 847484-(3,4-Dimethoxyphenyl)but-3-en-2-oneYield 17.75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3, 4-dimethoxybenzaldehyde (8.31 g, 50 mmol) in acetone (25 ml) and 95% ethanol (25 ml) was added water (200 ml) under stirring. During this time white precipitated solid was formed, and 10% sodium hydroxide aqueous solution (40 ml) was added dropwise under stirring below 10° C. Then the reaction mixture was stirred for 24 hr at room temperature, after the reaction completed, the reaction mixture was neutralized with 6N hydrochloric acid to adjust pH=7.0, the prepicitated yellow solid was collected by filtration and washed with ethanol, dried , then recrystallized from 95% ethanol to give 4.16 g of a pale yellow crystal, mp: 78-80° C., yield: 17.75%.

Workup

  1. customDuring this time white precipitated solid
  2. customwas formed
  3. stirringunder stirring below 10° C
  4. stirringThen the reaction mixture was stirred for 24 hr at room temperature
  5. filtrationthe prepicitated yellow solid was collected by filtration
  6. washwashed with ethanol
  7. customdried
  8. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-58ff3b5366694c5a9b29089b2dce39a1
Source dataset
uspto-grants-2013_09
Patent number
US08524744B2

Reaction notes

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