2'-Hydroxy-4'-methylacetophenone → 2-Ethyl-5-methylphenol

HRID 1453313

Reaction equation

HRID 1453313 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10]>CO.[Pd]>[CH2:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1])[CH3:10]

Participants

4

Reactant 1

HCID 813382'-Hydroxy-4'-methylacetophenone

Product 1

HCID 155232-Ethyl-5-methylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(2-hydroxy-4-methyl-phenyl)-ethanone (5 g, 33.3 mmol) and 10 wt % Pd/C (2 g, Degussa type) in MeOH (50 mL) was 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 a clear oil (4.5 g, 99%). 1H NMR (400 MHz, CDCl3): δ 1.23 (t, J=7.6 Hz, 3H), 2.27 (s, 3H), 2.59 (q, J=7.6 Hz, 2H), 4.68 (s, 1H), 6.59 (s, 1H), 6.71 (d, J=7.7 Hz, 1H), 7.01 (d, J=7.7 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashing with EtOAc
  3. concentrationThe filtrate was concentrated to a clear oil (4.5 g, 99%)

Sources & evidence

ORD record
ord-5c40fda8b53c4921941afd1b2abcbe54
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Linked notes

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