Cinnamoylbenzene → Dihydrochalcone

HRID 990892

Reaction equation

HRID 990892 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>C(OCC)(=O)C.[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

4

Reactant 1

HCID 7189Cinnamoylbenzene

Product 1

HCID 64802Dihydrochalcone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(42) Chalcone (2.00 g, 9.60 mmol) dissolved in 24 ml of ethyl acetate was hydrogenated with 100 mg of 10% Pd/C at 55 psi for 2 hours at room temperature. The catalyst was filtered through celite, and the solvent evaporated to give the crude product, which was chromatographed on silica gel using 4:1 hexanes:ethyl acetate yielding 1.20 g (60.0%) of a white, flaky powder. 1H NMR (250 MHz) δ 8.00-7.97 (m, 2H), 7.61-7.21 (m, 8H), 3.36-3.30 (t, 2H), 3.13-3.07 (t, 2H); 13C NMR (62.7 MHz) 199.4, 141.5, 137.0, 133.3, 128.8, 128.6, 128.2, 126.3, 40.6 ppm.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-71eaba5944514f399431420e8ff9fd23
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Linked notes

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