Acetone → 1,5-Bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one

HRID 1701137Notes

Reaction equation

HRID 1701137 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[F:5][C:6]([F:17])([F:16])[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[OH-:18].[Na+]>CO>[F:5][C:6]([F:16])([F:17])[O:3][C:2]1[CH:4]=[CH:12][C:11]([CH:10]=[CH:9][C:8](=[O:18])[CH:15]=[CH:12][C:11]2[CH:14]=[CH:15][C:8]([O:7][C:6]([F:17])([F:16])[F:5])=[CH:9][CH:10]=2)=[CH:14][CH:1]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 69573p-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 543760901,5-Bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-oneYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Acetone (8.7 g; 0.15 mole) is added to a solution of p-trifluoromethoxybenzaldehyde (57.0 g; 0.30 mole) in methanol (200 ml). The solution is cooled to 20° C. and 10% aqueous sodium hydroxide (8 ml) is added dropwise in about 5 minutes. The reaction mixture is then stirred at room temperature for 1.5 to 2 hours. During this period a yellow solid precipitates from the solution. The mixture is chilled overnight, filtered and the isolated yellow solid dried to afford 24.8 g (41%) of title product, m.p. 121°-123° C. NMR (acetone-d6) [δ=7.0-8.0 (M, 12H, aromatics and vinyl)]; IR 1590-1650 cm-1 (several bands).

Workup

  1. customDuring this period a yellow solid precipitates from the solution
  2. temperatureThe mixture is chilled overnight
  3. filtrationfiltered
  4. customthe isolated yellow solid dried

Sources & evidence

ORD record
ord-76e593ff1a774628a17c48a7e354f5bc
Source dataset
uspto-grants-1980_03
Patent number
US04191768

Reaction notes

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