Iodoethane → 2-(2-Ethoxyphenyl)ethanol

HRID 1985394Notes

Reaction equation

HRID 1985394 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[CH2:11](I)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6])[CH3:12]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 822002-(2-Hydroxyethyl)phenol

Product 1

HCID 2512712-(2-Ethoxyphenyl)ethanolYield 60.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.4 g of 2-hydroxyphenethyl alcohol was dissolved in 80 ml of N,N-dimethylformamide, and 15.3 g of ethyl iodide and 4.7 g of potassium carbonate were added. After stirring was continued at 70° C. overnight, the solution was diluted with ethyl acetate, and washed successively with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 3.2 g of the title compound in the 4:1 hexane-ethyl acetate fraction.

Workup

  1. washwashed successively with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-86837c17c97d48918aa2039672105904
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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