2-Fluoro-6-(1-hydroxyethyl)phenol → 2-Ethyl-6-fluorophenol

HRID 1453090Notes

Reaction equation

HRID 1453090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](O)[CH3:9])[C:3]=1[OH:11]>CO.[Pd]>[CH2:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[OH:11])[CH3:9]

Participants

4

Reactant 1

HCID 450831602-Fluoro-6-(1-hydroxyethyl)phenol

Product 1

HCID 587626932-Ethyl-6-fluorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-fluoro-6-(1-hydroxy-ethyl)-phenol (1.7 g, 10.9 mmol) and 10 wt % Pd/C (0.85 g, Degussa type) in MeOH (30 mL) was stirred under a balloon of H2 for 6 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to a yellow oil (1.35 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3H), 2.68 (q, J=7.3 Hz, 2H), 5.12 (s, 1H), 6.76 (m, 1H), 6.92 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashing with EtOAc
  3. concentrationThe filtrate was concentrated to a yellow oil (1.35 g, 87%)

Sources & evidence

ORD record
ord-ac9970a4d50c4411835a1f38bec020c4
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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