2'-Hydroxyacetophenone → Cinnamoylbenzene

HRID 2370483Notes

Reaction equation

HRID 2370483 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].C(O[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)C=C.[OH-].[K+]>>[C:18]1([CH:19]=[CH:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)=[O:10])[CH:21]=[CH:22][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 14797Potassium HydroxideHCID 959424-(Allyloxy)benzaldehyde

Product 1

HCID 7189Cinnamoylbenzene

Procedure

General procedure for the synthesis of chalcone 32a-l: To a round-bottom flask was charged with 2′-hydroxyacetophenone 31 (1.0 equiv.), 4-allyloxybenzaldehyde (1.0 equiv.) and excess potassium hydroxide solution (3M solution in 96% EtOH). The mixture was stirred at room temperature for 16 h. When TLC indicated complete consumption of 2′-hydroxyacetophenone, the reaction mixture was acidified to pH 5 with 1 M HCl solution at ice-bath temperature. The mixture was continuously extracted with CH2Cl2 (30 mL×3). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure to give a crude mixture, which was washed with 5% ethyl acetate in hexane to furnish desired chalcone.

Workup

  1. customconsumption of 2′-hydroxyacetophenone
  2. customthe reaction mixture was acidified to pH 5 with 1 M HCl solution at ice-bath
  3. extractionThe mixture was continuously extracted with CH2Cl2 (30 mL×3)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a crude mixture, which
  8. washwas washed with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d86f90cf9ac74383a6c6040a49c3b92f
Source dataset
uspto-grants-2014_04
Patent number
US08710097B2

Reaction notes

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