Water → Cinnamoylbenzene

HRID 2109511Notes

Reaction equation

HRID 2109511 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].O>CO>[C:4]1([CH:1]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7410AcetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 7189Cinnamoylbenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of an acetophenone in methanol (10 mL/mmol) was added an aldehyde (1.5 equiv) followed by an aqueous solution of KOH (50%, 1 mL/mmol of acetophenone). The mixture was heated at 70° C. for 4-6 hours and monitored by TLC. Water (20 mL) was then added, the methanol was evaporated, and the solution was extracted with CH2Cl2. The organic layer was dried and evaporated to dryness, then purified by recrystallization with methanol-water to afford the desired chalcone.

Workup

  1. customthe methanol was evaporated
  2. extractionthe solution was extracted with CH2Cl2
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. custompurified by recrystallization with methanol-water

Sources & evidence

ORD record
ord-e2a63b6ac8554d89878453481abe5418
Source dataset
uspto-grants-2009_04
Patent number
US07514579B2

Reaction notes

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