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

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

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%).