4-Fluorobenzaldehyde → 4-(4-Fluorophenyl)-1,1-diphenyl-3-buten-2-one

HRID 1720736Notes

Reaction equation

HRID 1720736 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]1([CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH3:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC[O-].[Na+]>CCO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:19][C:17](=[O:18])[CH:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 699071,1-DiphenylacetoneHCID 2723922Sodium ethoxide

Product 1

HCID 541471124-(4-Fluorophenyl)-1,1-diphenyl-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4-fluorobenzaldehyde (3.54 gm, 28.5 mmol) and 1,1-diphenylacetone (5.000 gm, 23.8 mmol) in absolute EtOH (50 ml) was treated with a solution of EtONa in EtOH (21% solution, 900 μl, 2.4 mmol). After stirring at room temperature for 22 hours, the mixture was concentrated to 35 ml and the solution was treated with HOAc (200 mg). The solution was cooled to 0° C. and the precipitate that had formed was collected by filtration and washed with cold EtOH. The title compound was obtained as a pale yellow solid (5.787 gm, 77%).

Workup

  1. concentrationthe mixture was concentrated to 35 ml
  2. additionthe solution was treated with HOAc (200 mg)
  3. temperatureThe solution was cooled to 0° C.
  4. customthe precipitate that had formed
  5. filtrationwas collected by filtration
  6. washwashed with cold EtOH

Sources & evidence

ORD record
ord-4672aafb982e44a6bb1801223e5321bf
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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