Acetone → 1,5-Bis[4-(dimethylamino)phenyl]-1,4-pentadien-3-one

HRID 2222260Notes

Reaction equation

HRID 2222260 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[CH3:5][N:6]([CH3:15])[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Cl-].[Na+].O>[CH3:5][N:6]([CH3:15])[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH:1][C:2](=[O:3])[CH:4]=[CH:11][C:10]2[CH:13]=[CH:14][C:7]([N:6]([CH3:15])[CH3:5])=[CH:8][CH:9]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2913771,5-Bis[4-(dimethylamino)phenyl]-1,4-pentadien-3-oneYield 22%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1.0 g (17.22 mmol) of acetone and 5.26 g (35.30 mmol) of 4-dimethylamino benzaldehyde in 172 mL of a 0.25M solution of aqueous NaOH (43.05 mmol) was added 2.26 mL (1.72 mmol) of a 25% w/w aqueous solution of cetyltrimethylammonium chloride. The mixture was allowed to stir vigorously at room temperature for 72 hours, diluted with 100 ml of brine and extracted with two 75 mL portions of methylene chloride. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was recrystallized from ethyl acetate to provide 1.21 g (22%) of a dark red powder.

Workup

  1. extractionextracted with two 75 mL portions of methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0e90ad36900f415797cffdc2eaa272b2
Source dataset
uspto-grants-2008_05
Patent number
US07371766B2

Reaction notes

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