Acetone → 1,4-Pentadien-3-one, 1,5-bis[4-(diethylamino)phenyl]-

HRID 647212Notes

Reaction equation

HRID 647212 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[CH3:14][C:15]([CH3:17])=[O:16].[OH-].[Na+]>C(O)C>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:14][C:15]([CH:17]=[CH:8][C:7]2[CH:10]=[CH:11][C:4]([N:3]([CH2:1][CH3:2])[CH2:12][CH3:13])=[CH:5][CH:6]=2)=[O:16])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 671144-(Diethylamino)benzaldehyde

Product 1

HCID 1085531,4-Pentadien-3-one, 1,5-bis[4-(diethylamino)phenyl]-Yield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 25 ml of anhydrous ethanol were dissolved 17.7 g of p-diethylaminobenzaldehyde and 2.9 g of acetone, and 1.5 ml of 10% aqueous NaOH was added dropwise to the resulting solution, after which the resulting mixture was subjected to reaction under reflux for 8 hours. The reaction mixture was cooled, and the crystals thus precipitated were collected by filtration and then recrystallized from toluene, to obtain 7.7 g of 1,3-bis(4'-diethylaminobenzal)acetone (m.p. 168° C.).

Workup

  1. additionwas added dropwise to the resulting solution
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 8 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe crystals thus precipitated
  6. filtrationwere collected by filtration
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e5520f18973d488591d3a66c275180af
Source dataset
uspto-grants-1983_10
Patent number
US04407927

Reaction notes

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