HCID 18701949, compound → 4-(Benzyloxy)-2-propylphenol

HRID 1609949Notes

Reaction equation

HRID 1609949 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[OH:18])[CH:2]=[CH2:3].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][C:5]([OH:18])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 18701949HCID 18701949, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 222611274-(Benzyloxy)-2-propylphenolYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Allyl-4-benzyloxyphenol (WO 9728137 A1 19970807, Adams, A. D. et al.) (5.00 g, 20.8 mmol) in ethyl acetate (40 mL) was treated with 5% Pd/C (0.25 g) and hydrogen (1 atm) at ambient temperature for 18 h. The mixture was filtered and concentrated. The crude product was purified on a Biotage medium pressure chromatography system using a 40L normal phase cartridge and eluted with 10% ethyl acetate in hexanes to give a tan solid (2.8 g, 56%). Rf=0.33 (25% EtOAc/Hexanes); 1H NMR (400 MHz, CDCl3) δ 7.44-7.31 (m, 5H), 6.78 (s, 1H), 6.69 (d, J=1.5 Hz, 2H), 5.00 (S, 2H), 4.31 (s, 1H), 2.55 (t, J=7.6 Hz, 2H), 1.64 (q, J=7.5 Hz, 2H), 0.97 (t, J=7.3 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified on a Biotage medium pressure chromatography system
  4. washeluted with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-388c33ab5e5947d48617450f80443333
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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