Ethyl Acetate → 3-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)propan-1-one

HRID 426392Notes

Reaction equation

HRID 426392 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CCOC(C)=O>[Pd].CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 27716653-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one

Product 1

HCID 27716663-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)propan-1-oneYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

A solution of 3,4- Dimethoxy-3′-hydroxy chalcone (4) (10 g, 35.2 mmol) in a 1:1 mixture of EtOAc:Acetone (40 mL) was treated with 10% Pd on Carbon (500 mg) and the mixture hydrogenated at 40-50 psi pressure of H2 for 3 h. The reaction mixture was filtered through a pad of Celite with the aid of acetone and the filtrate concentrated to afford a crude solid. The crude solid was triturated with EtOAc and filtered to afford 7.83 g (78%) of white solids which proved to be of ˜90% purity by 1H NMR analysis: 1H NMR (CDCl3, 300 MHz) 7.56 (s, 1H), 7.55, (d, J=2.2 Hz, 1H), 7.53-7.33 (m, 1H), 7.10 (dd, J=7.9, 2.4 Hz, 1H), 6.80-7.79 (m, 3H), 6.61 (s, 1H), 3.86 (s, 3H), 3.86 (s, 3H), 3.28 (t, J=7.9 Hz, 2H); 13C NMR (CDCl3, 75 MHz) 200.6, 156.9, 149.3, 147.8, 138.6, 134.2, 130.3, 121.1, 120.6, 115.0, 112.4, 111.8, 56.3, 41.2, 30.3.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite with the aid of acetone
  2. concentrationthe filtrate concentrated
  3. customto afford a crude solid
  4. customThe crude solid was triturated with EtOAc
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7c56d811b4e843fc8aa8dd8f668e1382
Source dataset
uspto-grants-2012_01
Patent number
US08106191B2

Reaction notes

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