1-Propanone, 1-(2-hydroxyphenyl)-3-phenyl- → Cinnamoylbenzene

HRID 1019452Notes

Reaction equation

HRID 1019452 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2O)=[O:10])=[CH:5][CH:6]=1>[Pd]>[C:4]1([CH:7]=[CH:8][C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 770521-Propanone, 1-(2-hydroxyphenyl)-3-phenyl-

Product 1

HCID 7189Cinnamoylbenzene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Hydrogenation of 1.06 g (4.38 mmol) of chalcone with catalytic amount of 10% Pd/C gives the dihydrochalcone after purification on silica gel chromatography. 1H NMR (300 MHz, CD3OD): δ 7.91 (d, d, J=1.8, 8.4 Hz, 1H), 7.50 (d, d, d, J=1.8, 7.2, 9.0 Hz, 1H), 6.97-6.92 (m, 2H), 5.83 (s, 1H), 3.34 (t, J=7.8 Hz, 2H), 2.96 (t, J=7.2 Hz, 2H), 2.13 (s, 3H); 1.87 (s, 3H).

Sources & evidence

ORD record
ord-36606c28fbfe43aeb13d3e953cf0ee22
Source dataset
uspto-grants-2014_05
Patent number
US08715761B2

Reaction notes

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