Paeonol → 2-Ethyl-5-methoxyphenol

HRID 1438226Notes

Reaction equation

HRID 1438226 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH3:10])=[C:5]([OH:12])[CH:4]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[C:5]([OH:12])[CH:4]=1

Participants

4

Reactant 1

HCID 11092Paeonol

Product 1

HCID 125297512-Ethyl-5-methoxyphenolYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(4-Methoxy-2-hydroxy-phenyl)-ethanone (11.0 g) was dissolved in MeOH (100 mL), treated with 10 wt % Pd/C (4.0 g, Degussa type) and stirred under a balloon of H2 for 24 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to give the product as an oil (10.0 g). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.85 Hz, 3H) 2.60- (q, J=6.22 Hz 2H), 3.75 (s, 3H), 6.40 (dd, J=9.04 Hz, 2.64 Hz, 1H), 6.45 (d, J=2.64 Hz, 1H) 7.00 (d, J=8.29 Hz, 1H), 12.90 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashing with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3c9a15d42fd647cb8c3cd7aa0b6407d8
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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