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

HRID 77652Notes

Reaction equation

HRID 77652 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:12][C:13]([CH3:15])=[O:14].[OH-].[Na+].O>C(O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:12][C:13](=[O:14])[CH:15]=[CH:7][C:6]2[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2913771,5-Bis[4-(dimethylamino)phenyl]-1,4-pentadien-3-oneYield 51.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Dimethylaminobenzaldehyde (1g, 1.00 g, 6.7 mmol) and acetone (19, 0.24 ml, 3.2 mmol) were combined in ethanol (10 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.40 g, 10 mmol) and water (10 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 0.53 g (51%) of an orange solid: mp 179-181° C. [expected mp 174-176° C.]; 1H NMR: δ 3.01 (s, 12H), 6.69 (d, 4H, J=8.7 Hz), 6.87 (d, 2H, J=15.7 Hz), 7.50 (d, 4H, J=8.7 Hz), 7.67 (d, 2H, J=15.7 Hz); 13C NMR: δ 40.2, 98.9, 111.8, 121.2, 122.9, 129.9, 142.8, 151.6.

Workup

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-bb2806f6fe994ae293200c31c4ccf657
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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