Acetophenone → 4-Dimethylaminochalcone

HRID 1612619Notes

Reaction equation

HRID 1612619 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:10][N:11]([CH3:20])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[OH-].[Na+]>CO.[Al]>[C:4]1([C:1](=[O:3])[CH:2]=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([N:11]([CH3:20])[CH3:10])=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 952974-Dimethylaminochalcone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5359268AluminumSolvent

Procedure

Acetophenone (28.0 g, 0.15 mole) and 4-dimethylaminobenzaldehyde (22.35 g, 0.15 mole) were dissolved in methanol (150 ml) in a 500 ml, 3-necked round bottom flask. The flask was wrapped in aluminium foil to exclude light and was fitted with a mechanical stirrer and a water cooled condenser. The third neck was stoppered and used to obtain samples for monitoring during the reaction. Aqueous sodium hydroxide solution (50 ml of 30% w/v) was added dropwise to the vigorously stirred clear methanolic solution. A yellow/orange solid started separating from the reaction solution (which had turned orange) after about 24 hours. Stirring was continued for about 48 hours at ambient temperature and the intermediate title compound was isolated by vacuum filtration, washed successively with water, methanol and petroleum ether (40-60° C.) and dried in vacuo to give 23.3 g (62% of theory) of 1-phenyl-3-(4-dimethylaminophenyl)-1-oxo-prop-2-ene with a melting point of 112-114° C.

Workup

  1. customwas fitted with a mechanical stirrer and a water cooled condenser
  2. customto obtain samples for monitoring
  3. customduring the reaction
  4. customA yellow/orange solid started separating from the reaction solution (which had turned orange) after about 24 hours

Sources & evidence

ORD record
ord-389903cbbb2e44af9e2a43173c47ad1c
Source dataset
uspto-grants-1993_03
Patent number
US05190909

Reaction notes

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