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

HRID 77661Notes

Reaction equation

HRID 77661 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-2815bcc91030459faaf379969d6f315b
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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