Acetone → 1,5-Bis(p-chlorophenyl)-1,4-pentadien-3-one

HRID 77659Notes

Reaction equation

HRID 77659 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:10][C:11](=[O:12])[CH:13]=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2299341,5-Bis(p-chlorophenyl)-1,4-pentadien-3-oneYield 70.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chlorobenzaldehyde (1x, 1.00 g, 7.1 mmol) and acetone (19, 0.26 ml, 3.5 mmol) were combined in ethanol (10 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.40 g, 10.0 mmol) and water (10 ml) was added and the mixture stirred for 3 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate to give 0.75 g (70%) of yellow crystals: mp 187-189° C. [expected mp 191-193° C.]; 1H NMR: δ 7.00 (d, 2H, J=15.9 Hz), 7.37 (d, 4H, J=8.5 Hz), 7.52 (d, 4H, J=8.5 Hz), 7.66 (d, 2H, J=15.9 Hz); 13C NMR: δ 125.7, 129.2, 129.5, 133.2, 136.4, 141.9, 188.1.

Workup

  1. stirringthe mixture stirred for 3 hr at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5bb269518561412d9bea3b2b452bc37f
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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