Acetone → (E)-4-(3-Chloro-4-cyclohexyl-phenyl)-3-butene-2-one

HRID 1605661Notes

Reaction equation

HRID 1605661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH:5]=O.[CH3:16][C:17]([CH3:19])=[O:18].CO.[OH-].[K+]>O>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:16]/[C:17](=[O:18])[CH3:19])[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 14797Potassium HydroxideHCID 107277773-Chloro-4-cyclohexylbenzaldehyde

Product 1

HCID 21547138(E)-4-(3-Chloro-4-cyclohexyl-phenyl)-3-butene-2-oneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

222.72 Gm (1.0 mol) of 3-chloro-4-cyclohexyl-benzaldehyde, 3,500 gm (60.3 mols) of acetone and 200 ml of methanol were charged into a 6-liter three-necked flask equipped with a stirrer, dropping funnel and internal thermometer. While thoroughly stirring the contents of the flask, a solution of 2.805 gm (0.05 mol) of potassium hydroxide in 16 ml of water was added dropwise thereto, while an internal temperature of 20° to 25°C was maintained. The mixture was then stirred for 3 hours more. The precipitate solid by-product was filtered off, and the filtrate was neutralized by dropwise addition of glacial acetic acid, and concentrated by evaporation in vacuo. The residue was shaken with a mixture of water and ether. The ether phase separated, dried over sodium sulfate, clarified with charcoal, and evaporated. The residual oil was distilled in a high vacuum (b.p. 162°-175°C at 0.2 mm Hg), crystallized by trituration with a small quantity methanol, and finally recrystallized once from methanol. The colorless crystals melted at 48°-49°C. Yield: 40 % of theory.

Workup

  1. customequipped with a stirrer
  2. temperaturewhile an internal temperature of 20° to 25°C was maintained
  3. stirringThe mixture was then stirred for 3 hours more
  4. filtrationThe precipitate solid by-product was filtered off
  5. additionthe filtrate was neutralized by dropwise addition of glacial acetic acid
  6. concentrationconcentrated by evaporation in vacuo
  7. stirringThe residue was shaken with a mixture of water and ether
  8. customThe ether phase separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. distillationThe residual oil was distilled in a high vacuum (b.p. 162°-175°C at 0.2 mm Hg)
  12. customcrystallized by trituration with a small quantity methanol
  13. customfinally recrystallized once from methanol

Sources & evidence

ORD record
ord-43a8c2c3185045ae9fc99a70f8f365e1
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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