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

HRID 1700719Notes

Reaction equation

HRID 1700719 reaction equation
[OH-].[Na+].O.[Cl:4][C:5]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:6]=1[CH:7]=O.[CH3:14][C:15]([CH3:17])=[O:16]>>[Cl:4][C:5]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:6]=1[CH:7]=[CH:14][C:15](=[O:16])[CH3:17]

Participants

5

Reactant 4

HCID 180Acetone2×HCID 962WaterHCID 14798Sodium HydroxideHCID 156472782-Chloro-5-methylbenzaldehyde

Product 1

HCID 541354784-(2-Chloro-5-methylphenyl)-3-buten-2-one

Procedure

To a mixture of acetone (160 ml), sodium hydroxide (2.6 g) and water (160 ml) was added dropwise at 0° C. a solution of crude 2-chloro-5-methylbenzaldehyde (18.3 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-(2-chloro-5-methylphenyl)-3-buten-2-one (18.9 g) as oil.

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-109ff9bfa5c14315b7ec696f64e3584d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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