Acetone → 1,4-Pentadien-3-one, 1,5-bis(3-chlorophenyl)-

HRID 77660Notes

Reaction equation

HRID 77660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:10][C:11](=[O:12])[CH:13]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 27759911,4-Pentadien-3-one, 1,5-bis(3-chlorophenyl)-Yield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chlorobenzaldehyde (1y, 2.00 ml, 17.7 mmol) and acetone (19, 0.65 ml, 8.8 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (20 ml) was added and the mixture stirred for 2 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate to give 2.41 g (90%) of a yellow solid: mp 125-127° C. [expected mp 120-121° C.]; 1H NMR: δ 7.03 (d, 2H, J=15.9 Hz), 7.33 (m, 4H), 7.45 (d, 2H, J=6.6 Hz), 7.58 (m, 2H), 7.64 (d, 2H, J=15.9 Hz); 13C NMR: δ 126.3, 126.6, 127.9, 130.1, 130.3, 134.9, 136.5, 141.8, 188.0.

Workup

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

Sources & evidence

ORD record
ord-2c6edeb83f5a4d36ad08b052ef281327
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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