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

HRID 77655Notes

Reaction equation

HRID 77655 reaction equation
[F: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>[F: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]([F:1])=[CH:3][CH:4]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 12682491,5-Bis(4-fluorophenyl)-1,4-pentadien-3-oneYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluorobenzaldehyde (1r, 0.75 ml, 7.0 mmol) and acetone (19, 0.26 ml, 3.5 mmol) were combined in ethanol (30 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.50 g, 12.5 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 ethanol to afford 0.82 g (86%) of a yellow solid: mp 150-152° C. [expected mp 152-154° C.]; 1H NMR: δ 6.97 (d, 2H, J=15.9 Hz), 7.09 (m, 4H), 7.58 (m, 4H), 7.68 (d, 2H, J=15.9 Hz); 13C NMR: δ 116.1, 1125.1, 130.2, 130.9, 142.0, 164.0, 188.3.

Workup

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

Sources & evidence

ORD record
ord-3bed8c902b074631b95627bb269e3ec1
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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