Methyl iodide → 2-Methoxyphenethyl alcohol

HRID 725611

Reaction equation

HRID 725611 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[C:11]([O-])([O-])=O.[Cs+].[Cs+].CI>CC(C)=O>[OH:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 822002-(2-Hydroxyethyl)phenol

Product 1

HCID 819092-Methoxyphenethyl alcohol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 10 g of 2-(2-hydroxyphenyl)-ethanol in 200 ml of acetone there are added 35.3 g of Cs2CO3 and then a solution of 6.5 ml of methyl iodide in 40 ml of acetone. The reaction mixture is stirred for 50 minutes at more temperature, is filtered and is concentrated by evaporation. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (dichloromethane/diethyl ether=97:3), yielding the title compound: Rf (dichloromethane/diethyl ether=97:3)=0.34; HPLC Rt =9.31 minutes.

Workup

  1. filtrationis filtered
  2. concentrationis concentrated by evaporation
  3. customThe residue is partitioned between diethyl ether and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customthe residue is purified by means of FC (dichloromethane/diethyl ether=97:3)

Sources & evidence

ORD record
ord-22df3bb292f24ab5a7281b46f6a59137
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Linked notes

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