1-(4-ethoxy-2-hydroxyphenyl)ethanone → HCID 58764267, compound

HRID 859634Notes

Reaction equation

HRID 859634 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[C:6]([OH:13])[CH:5]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([OH:13])[CH:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 27751631-(4-ethoxy-2-hydroxyphenyl)ethanone

Product 1

HCID 58764267HCID 58764267, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(4-Ethoxy-2-hydroxy-phenyl)-ethanone was dissolved in MeOH (40 mL), treated with 10 wt % Pd/C (1.4 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 (3.12 g, 97%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.6 Hz, 3 H), 1.39 (t, J=7.1 Hz, 3 H), 2.56 (d, J=7.6 Hz, 2 H), 3.98 (d, J=7.1 Hz, 2 H), 4.79 (s, 1 H), 6.37 (d, J=2.5 Hz, 1 H), 6.44 (dd, J=8.3, 2.5 Hz, 1 H), 7.01 (d, J=8.3 Hz, 1 H).

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-6d2b56f0c9d4497b9be566da8ba2d8ed
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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