Acetone → 1,5-Bis(2-chlorophenyl)-1,4-pentadien-3-one

HRID 714176Notes

Reaction equation

HRID 714176 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:10][C:11](=[O:12])[CH:13]=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 69962-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2193691,5-Bis(2-chlorophenyl)-1,4-pentadien-3-oneYield 67.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chlorobenzaldehyde (1z, 2.00 ml, 17.8 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 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate to give 1.80 g (67%) of a yellow solid: mp 119-121° C. [expected mp 110° C.]; 1H NMR: δ 7.04 (d, 2H, J=16.1 Hz), 7.29 (m, 4H), 7.41 (m, 2H), 7.67 (m, 2H), 8.11 (d, 2H, J=16.1 Hz); 13C NMR: δ 127.0, 127.5, 127.6, 130.1, 131.1, 132.9, 135.3, 139.2, 188.4.

Workup

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-427f40d2f8eb48159c92b6c1c5b20ad5
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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