Acetone → 2-Chlorobenzylideneacetone

HRID 46493Notes

Reaction equation

HRID 46493 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[OH-].[Na+].Cl.[CH3:13][C:14]([CH3:16])=[O:15]>O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:13][C:14](=[O:15])[CH3:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 69962-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 1407602-ChlorobenzylideneacetoneYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 200 g (1.4 mole) of 2-chlorobenzaldehyde in 500 ml of acetone is treated with 200 ml of water, cooled in an ice bath, then treated with 40 ml of 10% NaOH by drops. The mixture is kept below 40° C. After the addition is complete the mixture is stirred at 25° C. for 1.5 hours, then acidified with 10% HCl. The mixture is diluted with water and extracted with benzene. 0.5 g of toluene-sulfonic acid is added to the benzene solution and the mixture refluxed under a water separator. A total of 6 ml of water is collected. The mixture is cooled, shaken with bicarbonate, dried (Na2SO4), and evaporated. Distillation gives 150 g (60%) of 4-(2-chlorophenyl)-but-3-ene-2-one, b.p. 106°-120° C. @ 1 mm Hg.

Workup

  1. temperaturecooled in an ice bath
  2. customis kept below 40° C
  3. additionAfter the addition
  4. extractionextracted with benzene
  5. addition0.5 g of toluene-sulfonic acid is added to the benzene solution
  6. temperaturethe mixture refluxed under a water separator
  7. customA total of 6 ml of water is collected
  8. temperatureThe mixture is cooled
  9. stirringshaken with bicarbonate
  10. dry with materialdried (Na2SO4)
  11. customevaporated
  12. distillationDistillation

Sources & evidence

ORD record
ord-6cb13f5be3f344e2af074da8b7aaf079
Source dataset
uspto-grants-1979_11
Patent number
US04173649

Reaction notes

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