2-Methoxy-4-Methylphenol → 2-Methoxy-1-(3-methoxy-propoxy)4-methyl-benzene

HRID 1158455Notes

Reaction equation

HRID 1158455 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10].Br[CH2:12][CH2:13][CH2:14][O:15][CH3:16].C([O-])([O-])=O.[K+].[K+]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[O:10][CH2:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

4

Reactant 3

HCID 71442-Methoxy-4-MethylphenolHCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 577907582-Methoxy-1-(3-methoxy-propoxy)4-methyl-benzene

Procedure

A stirred solution of 2-methoxy-4-methylphenol (5.00 g, 36.2 mmol), 1-bromo-3-methoxypropane (7.06 g, 45.2 mmol) and anhydrous K2CO3 (7.50 g, 64.3 mmol) is refluxed overnight. After cooling, volatiles are removed under reduced pressure, the residue is taken up in water and extracted with AcOEt. The combined organics are washed with brine, dried (Na2SO4) and concentrated. After silica gel chromatography (hexane/AcOEt 3:1) the title compound is obtained as colorless liquid. TLC, Rf (hexane/AcOEt 2:1)=0.34. MS: 211.0 [M+H]+. 1H-NMR (CDCl3): δ 2.13 (m, 2H), 2.33 (s, 3H), 3.38 (s, 3H), 3.61 (m, 2H), 3.88 (s, 3H), 4.12 (m, 2H), 6.7-6.85 (m, 3H) ppm.

Workup

  1. temperatureAfter cooling
  2. customvolatiles are removed under reduced pressure
  3. extractionextracted with AcOEt
  4. washThe combined organics are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3d35366d7b1485bb172687988d8921f
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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