Potassium Carbonate → 4-Methoxy-3-(3-methoxypropoxy)benzenemethanol

HRID 2256752Notes

Reaction equation

HRID 2256752 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][O:22][CH3:23].C(OCC)(=O)C.CCCCCC>CC(C)=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][OH:6])=[CH:3][C:2]=1[O:1][CH2:19][CH2:20][CH2:21][O:22][CH3:23]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 780893-Hydroxy-4-methoxybenzyl alcoholHCID 5245511-Bromo-3-methoxypropaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7.7 g of 3-hydroxy-4-methoxy-benzyl alcohol, 10.35 g of potassium carbonate and 12.1 g of 1-bromo-3-methoxy-propane are stirred under reflux in 150 ml of acetone for 3 days. After evaporation of the solvent, water is added to the residue and extraction is carried out with ethyl acetate. After evaporation of the solvent the title compound is obtained from the organic extracts by means of FC (240 g of silica gel, dichloromethane/methanol=96:4): Rf (ethyl acetate/hexane=2:1)=0.31.

Workup

  1. customAfter evaporation of the solvent, water
  2. additionis added to the residue and extraction
  3. customAfter evaporation of the solvent the title compound
  4. customis obtained from the organic extracts by means of FC (240 g of silica gel, dichloromethane/methanol=96:4)

Sources & evidence

ORD record
ord-593a0927cb82461f864a873f3267d324
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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