Ethylene Glycol → 2-(Benzyloxy) ethanol

HRID 2183431Notes

Reaction equation

HRID 2183431 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[OH-].[Na+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[CH2:7]([O:3][CH2:2][CH2:1][OH:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 121412-(Benzyloxy) ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Ethylene glycol (742.5 g, 11.96 mol) was added to a solution of sodium hydroxide pellets (475.2 g, 11.88 mol) in 450 ml of water kept at 80° C. Benzyl chloride (302.8 g, 2.39 mol) was then added at 65° C., and the resulting suspension was vigorously stirred at 120° C. overnight. After cooling to room temperature, the mixture was poured into ice-water and extracted five times with diethyl ether. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The remaining residue was then distilled under vacuum and the relevant fractions (bp. 95-125° C. at 0.1-1 mbar) collected.

Workup

  1. customkept at 80° C
  2. temperatureAfter cooling to room temperature
  3. extractionextracted five times with diethyl ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe remaining residue was then distilled under vacuum
  9. customthe relevant fractions (bp. 95-125° C. at 0.1-1 mbar) collected

Sources & evidence

ORD record
ord-2f09fa30514d4768978d355b64db2cd4
Source dataset
uspto-grants-2005_05
Patent number
US06900194B1

Reaction notes

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