Acetone → 4-(5-Fluoro-2-methylphenyl)-3-buten-2-one

HRID 49189Notes

Reaction equation

HRID 49189 reaction equation
[OH-].[Na+].O.[F:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:13])=[C:9]([CH:12]=1)[CH:10]=O.[CH3:14][C:15]([CH3:17])=[O:16]>>[F:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:13])=[C:9]([CH:10]=[CH:14][C:15](=[O:16])[CH3:17])[CH:12]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 962WaterHCID 14798Sodium HydroxideHCID 27590125-Fluoro-2-methylbenzaldehyde

Product 1

HCID 540396424-(5-Fluoro-2-methylphenyl)-3-buten-2-one

Procedure

A mixture of acetone (80 ml), sodium hydroxide (3.7 g) and water (100 ml) was treated at room temperature dropwise with a solution of 5-fluoro-2-methylbenzaldehyde (11.5 g) in acetone (30 ml) and stirred at the same temperature for 1 hour. Acetone was distilled off under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine and concentrated under reduced pressure to obtain 4-(5-fluoro-2-methylphenyl)-3-buten-2-one (13.4 g).

Workup

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

Sources & evidence

ORD record
ord-79e6aaa0f0ab48a2bfc1ef78b562a897
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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