Acetone → 2-Chlorobenzylideneacetone

HRID 1700523Notes

Reaction equation

HRID 1700523 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O.[CH3:12][C:13]([CH3:15])=[O:14]>>[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[CH:12][C:13](=[O:14])[CH3:15]

Participants

4

Reactant 3

HCID 180AcetoneHCID 69962-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 1407602-Chlorobenzylideneacetone

Procedure

To a mixed solution of acetone (294 ml) and an aqueous solution (1.4 l) of sodium hydroxide (22.0 g) was added 2-chlorobenzaldehyde (70.3 g), and the mixture was stirred at room temperature for 5 hours. Excess acetone was evaporated under reduced pressure, and to the residue was added ethyl acetate (1.4 l). The mixture was subjected to extraction, and the ethyl acetate layer was washed with brine and dried (anhydrous magnesium sulfate). Under reduced pressure, ethyl acetate was evaporated to give crude 2-chlorobenzalacetone (94.6 g) as yellow oil, which was used for the following reaction without further purification.

Workup

  1. customExcess acetone was evaporated under reduced pressure
  2. additionto the residue was added ethyl acetate (1.4 l)
  3. extractionThe mixture was subjected to extraction
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customUnder reduced pressure, ethyl acetate was evaporated

Sources & evidence

ORD record
ord-af6a7b13a7db4278bf12b038cc7ee97c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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