Methyl iodide → 2-Methoxyphenethyl alcohol

HRID 1452118Notes

Reaction equation

HRID 1452118 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].CI.O[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][OH:18]>CC(C)=O>[OH:18][CH2:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:4][CH3:1]

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

35.3 g of caesium carbonate and then a solution of 6.5 ml of methyl iodide in 40 ml of acetone are added to a solution of 10 g of 2-(2-hydroxyphenyl)-ethanol in 200 ml of acetone. The reaction mixture is stirred for 50 minutes at room temperature, filtered and 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) to yield the title compound: Rf (dichloromethane/diethyl ether 97:3)=0.34; HPLC Rt =9.31 minutes.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated 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-00a637908c974cad949c92b19236042d
Source dataset
uspto-grants-1997_02
Patent number
US05606078

Reaction notes

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