3-Hydroxybenzyl alcohol → 3-Ethoxybenzenemethanol

HRID 1169482Notes

Reaction equation

HRID 1169482 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].I[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6])[CH3:12]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 6340IodoethaneHCID 11430Potassium Carbonate

Product 1

HCID 41861833-EthoxybenzenemethanolYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-hydroxybenzyl alcohol (3.56 g) and acetone (100 ml) were added iodoethane (6.7 g) and potassium carbonate (7.9 g), and the resulting mixture was heated at reflux for 61 hours. The reaction mixture was concentrated, ethyl acetate was added to the residue and the resulting mixture was washed successively with water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 3-ethoxybenzyl alcohol (4.15 g) as an oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 61 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washthe resulting mixture was washed successively with water
  6. dry with materialan aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3423112be6ef4b428600c0fd0ff1872e
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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