Acetophenone → 3-(Dimethylamino)-1-phenyl-2-propen-1-one

HRID 1199941Notes

Reaction equation

HRID 1199941 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CCCCCC>[CH3:12][N:13]([CH3:15])[CH:14]=[CH:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 50.0 g of acetophenone and 150 ml of N,N-dimethylformamide dimethyl acetal was stirred and heated at reflux for 8 hours. The mixture was allowed to cool to room temperature, then the solvent was removed in vacuo to give a crystalline residue. The residue was treated with 400 ml of hexane then filtered. The material on the filter was washed with hexane to give 47.8 g of the desired product as yellow crystals, mp 88°-91° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. customthe solvent was removed in vacuo
  4. customto give a crystalline residue
  5. filtrationthen filtered
  6. washThe material on the filter was washed with hexane

Sources & evidence

ORD record
ord-dbc4a26741404ef68830f721f2f6fc1b
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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