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

HRID 714170Notes

Reaction equation

HRID 714170 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-5d5b295fe5da4ed990aced4200808cab
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

Loading…