Cinnamoylbenzene → Dihydrochalcone

HRID 488769

Reaction equation

HRID 488769 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1.CO.[Pd]>[C:11]1([C:9](=[O:10])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 1

HCID 7189Cinnamoylbenzene2×

Product 1

HCID 64802Dihydrochalcone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Chalcone (compound 1) (37.6 mmol) was dissolved in 250 ml of toluene (in some cases 25 ml of MeOH was added to insure a complete dissolution) and 400 mg of 10% Pd/C (0.01 eq) was added to the mixture. The compound was hydrogenated at 45 psi in a Parr apparatus for 40 min to 3 hrs to form 1,3-diphenylpropan-1-one (compound 2), during which time the reaction mixture was periodically checked for the starting material by TLC (Hex:EtOAc=1:1) to prevent over-reduction. Upon completion of reduction the reaction mixture was filtered through a short pad (2-3 inch) of silica gel and solvent was removed in vacuo to afford a crude product, which was either sufficiently pure to use in the next step or was purified by recrystallization from MeOH or Hex:EtOAc=3:1 or, in the case where over-reduction has occurred, by silica gel column chromatography using Hex:EtOAc=5:1 as an eluent.

Workup

  1. additionwas added
  2. additionwas added to the mixture
  3. waitThe compound was hydrogenated at 45 psi in a Parr apparatus for 40 min to 3 hrs

Sources & evidence

ORD record
ord-994b12f7f02b4285a88bc79c31b5961a
Source dataset
uspto-grants-2005_12
Patent number
US06974830B2

Linked notes

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