Potassium Hydroxide → 1,3-Diphenyl-2-propyn-1-one

HRID 1071760Notes

Reaction equation

HRID 1071760 reaction equation
[OH-].[K+].[CH:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](\Br)/[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:4]=1>O.O.CC(C)=O>[CH:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 5383396alpha-Bromochalcone

Product 1

HCID 976371,3-Diphenyl-2-propyn-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Potassium hydroxide (3.48 mmol), dissolved in water (0.87 M (4.0 ml)), is added over about 30 minutes to a refluxing solution of the alpha-bromochalcone (3.48 mmol) in 0.35 M of 1:1 water/acetone (5 ml each). After 20 minutes of further refluxing, the solution is cooled and diluted with water. The water is extracted with ether, which is dried with MgSO4 and evaporated. Chromatography on silica gel yielded 1,3-diphenylpropynone and its derivatives. VI. alpha-Tetralonylideneacetophenone Derivatives

Workup

  1. temperaturethe solution is cooled
  2. extractionThe water is extracted with ether, which
  3. dry with materialis dried with MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-91892963b0684dd5907003560b829306
Source dataset
uspto-grants-2005_06
Patent number
US06906105B2

Reaction notes

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