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

HRID 264945

Reaction equation

HRID 264945 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-09b73114d8df4a4c995dc3f4e81f87c6
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Linked notes

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