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

HRID 1779832Notes

Reaction equation

HRID 1779832 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-015ee9faa9cb4e05892c1336d1b873f1
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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