Ethylene Glycol → 2-(Benzyloxy) ethanol

HRID 248159Notes

Reaction equation

HRID 248159 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[OH-].[K+].[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 14797Potassium Hydroxide

Product 1

HCID 121412-(Benzyloxy) ethanolYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 156.75 g of dry ethylene glycol and 64.37 g of 87.2% potassium hydroxide is warmed and stirred until a complete solution. The mixture is then stirred in a 90° C. oil bath and 130.51 g of benzyl chloride is added dropwise over 2 hours. This mixture is then stirred at 130° C. for 2 hours, cooled and 500 ml of water added. The oil is extracted twice with ether. The extracts are combined and evaporated. The residue is distilled, giving 83.2 g of ethylene glycol monobenzyl ether.

Workup

  1. temperatureis warmed
  2. stirringThe mixture is then stirred in a 90° C. oil bath
  3. stirringThis mixture is then stirred at 130° C. for 2 hours
  4. temperaturecooled
  5. extractionThe oil is extracted twice with ether
  6. customevaporated
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-a0350f4627194723a11ee831d37dfbdd
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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