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

HRID 1108752Notes

Reaction equation

HRID 1108752 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.N1CC[CH2:16][CH2:15][CH2:14]1.C(O)(=[O:21])C>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:14][C:15](=[O:21])[CH3:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 8419Veratraldehyde

Product 1

HCID 847484-(3,4-Dimethoxyphenyl)but-3-en-2-oneYield 56.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,4-Dimethoxybenzaldehyde (30.1 g) was dissolved in acetone (900 ml), and then piperidine (23.2 ml) and acetic acid (13.4 ml) were added prior to reflux for 4 hours. After distilling off the reaction solvent under reduced pressure, it was dissolved in 600 ml of ethyl acetate and washed with saturated sodium bicarbonate water and saturated saline. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure producing yellow crystals which were then washed in isopropyl ether to give 21.0 g of 4-(3,4-dimethoxyphenyl)-3-buten-2-one (56.4%).

Workup

  1. temperatureto reflux for 4 hours
  2. distillationAfter distilling off the reaction solvent under reduced pressure, it
  3. dissolutionwas dissolved in 600 ml of ethyl acetate
  4. washwashed with saturated sodium bicarbonate water and saturated saline
  5. dry with materialAfter drying with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customproducing yellow crystals which
  8. washwere then washed in isopropyl ether

Sources & evidence

ORD record
ord-642f1bf43dfa4cbc9dbefaaeb23d6818
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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