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

HRID 1700714Notes

Reaction equation

HRID 1700714 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

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

Workup

  1. customUnder reduced pressure, acetone was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf8e065908ac478db9dae47735935d87
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…