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

HRID 253196

Reaction equation

HRID 253196 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.

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-4ba327e74c5243feaac8ef51b5912f6b
Source dataset
uspto-grants-2011_01
Patent number
US07872029B2

Linked notes

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