HCID 54123683, compound → HCID 54213211, compound

HRID 259928Notes

Reaction equation

HRID 259928 reaction equation
[CH2:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([OH:12])=[C:6]([F:13])[CH:5]=1)[CH:2]=[CH2:3]>CCO.[Pd]>[F:13][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[C:9]([O:10][CH3:11])=[CH:8][C:7]=1[OH:12]

Participants

4

Reactant 1

HCID 54123683HCID 54123683, compound

Product 1

HCID 54213211HCID 54213211, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

4-Allyl-2-fluoro-5-methoxyphenol (5.16 g, 28.3 mmol) was dissolved in EtOH (150 mL) and Pd/C (5%, 250 mg) was added. Hydrogenation for 6 h at room temperature and atmospheric pressure, addition of more Pd/C (5%, 100 mg), continued reaction for 3 h followed by removal of the catalyst and evaporation of the solvent gave 2-fluoro-5-methoxy-4-propylphenol (4.52 g) as an oil. 1H NMR (DMSO-d6): δ9.53 (s, 1H), 6.85 (d, J=11.8 Hz, 1H), 6.51 (d, J=7.7 Hz, 1H), 3.67 (s, 3H), 2.38 (t, J=7.5 Hz, 2H), 1.46 (m, J=7.5 Hz, 2H), 0.84 (t, J=7.4 Hz, 3H). 13C NMR (DMSO-d6): δ153.21, 144.84 (d, J=230 HZ), 142.70 (d, J=13 Hz), 120.41 (d, J=5 Hz), 116.46 (d, J=19 Hz), 101.25, 55.62, 30.68, 22.61, 13.71. MS (EI, 70 eV): m/z (rel. int.) 184 (M+, 69).

Workup

  1. customreaction for 3 h
  2. customfollowed by removal of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-bdb26459a68844d398699bfea135e038
Source dataset
uspto-grants-1996_06
Patent number
US05523475

Reaction notes

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