Acetone → 4-(2-Chloro-5-fluorophenyl)-3-buten-2-one

HRID 49196Notes

Reaction equation

HRID 49196 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]=O.[CH3:13][C:14]([CH3:16])=[O:15]>O>[Cl:3][C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]=[CH:13][C:14](=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 180Acetone2×HCID 14798Sodium HydroxideHCID 27791842-Chloro-5-Fluorobenzaldehyde

Product 1

HCID 539229184-(2-Chloro-5-fluorophenyl)-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.78 g) was dissolved in water (55 ml) and treated dropwise with acetone (55 ml) followed by a solution of 2-chloro-5-fluorobenzaldehyde (2.8 g) in acetone (10 ml). The reaction mixture was stirred at room temperature for 2 hours. Acetone was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and concentrated under reduced 5 pressure to obtain 4-(2-chloro-5-fluorophenyl)-3-buten-2-one (0.24 g).

Workup

  1. distillationAcetone was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. concentrationconcentrated under reduced 5 pressure

Sources & evidence

ORD record
ord-54bc9528b20642ac91a50a3cc2b0ba87
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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