Hydrochloric Acid → Cinnamoylbenzene

HRID 488768Notes

Reaction equation

HRID 488768 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>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 313Hydrochloric AcidHCID 7410AcetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 7189Cinnamoylbenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetophenone (0.05 mol) and aldehyde (0.05 mol) in 150 ml of MeOH was added 2.5 eq of NaOH as pellets. The reaction bottle was placed on a shaker (slightly exothermic reaction) for 24-48 hrs. Then the reaction container was placed in an acetone-ice bath (−5 to 0° C.) and the reaction mixture was quenched with 10.3 ml of 37% aqueous HCl (2.5 eq). Solvent was removed in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was discarded and the organic layer was washed with water, brine and dried over Na2SO4. Solvent was removed in vacuo and the crude chalcone (compound 1) was recrystallized from methanol (MeOH) or a mixture of hexane and ethyl acetate (Hex:EtOAc) 3:1 or purified by silica gel chromatography using a mixture of Hex:EtOAc=5:1 as an eluent.

Workup

  1. customslightly exothermic reaction) for 24-48 hrs
  2. customThen the reaction container was placed in an acetone-ice bath
  3. customSolvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc and water
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed in vacuo
  8. customthe crude chalcone (compound 1) was recrystallized from methanol (MeOH)
  9. additiona mixture of hexane and ethyl acetate (Hex:EtOAc) 3:1
  10. custompurified by silica gel chromatography
  11. additiona mixture of Hex

Sources & evidence

ORD record
ord-021fb76f76b64ff0a5653ed98dcb24ed
Source dataset
uspto-grants-2005_12
Patent number
US06974830B2

Reaction notes

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