Ethylene Glycol → 1,2-Diallyloxyethane ether

HRID 375601Notes

Reaction equation

HRID 375601 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH2:5](Br)[CH:6]=[CH2:7].[C:9]1([CH3:15])[CH:14]=CC=C[CH:10]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:5]([O:3][CH2:2][CH2:1][O:4][CH2:14][CH:9]=[CH2:10])[CH:6]=[CH2:7].[CH3:1][CH2:2][O:3][CH2:9][CH3:15]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 867492221,2-Diallyloxyethane etherYield 99%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Into a 500 mL round bottom three neck flask equipped with an overhead stirrer, thermometer, condenser and nitrogen inlet were placed 31 g (0.50 mol) of 1,2-ethanediol, 182 g (1.5 mol) of allyl bromide, 75 mL of toluene and 60 g (1.5 mole) of NaOH. The reaction mixture was stirred at room temperature for 15 minutes. Then 9 g (0.03 mole) of tetra-n-butylammonium bromide was added and the reaction mixture slowly heated to reflux (50°-60° C.) and maintained at that temperature overnight. The reaction mixture was poured into 500 mL of distilled water, the organic layers were separated and the aqueous layer extracted with fresh toluene. The combined organic layers were washed with three 200 mL portions of distilled water and the organic phase was dried over anhydrous Na2SO4. Excess allyl bromide and toluene were removed using a rotary evaporator and the reaction mixture was distilled under vacuum. The volatile product amounted to 53 g (74% recovered yield). Fractional distillation gave 99% pure 1,2-diallyloxyethane ether with a boiling point of 55° C./20 mm Hg.

Workup

  1. customInto a 500 mL round bottom three neck flask equipped with an overhead stirrer
  2. customthermometer, condenser and nitrogen inlet were placed
  3. temperaturethe reaction mixture slowly heated
  4. temperatureto reflux (50°-60° C.)
  5. temperaturemaintained at that temperature overnight
  6. customthe organic layers were separated
  7. extractionthe aqueous layer extracted with fresh toluene
  8. washThe combined organic layers were washed with three 200 mL portions of distilled water
  9. dry with materialthe organic phase was dried over anhydrous Na2SO4
  10. customExcess allyl bromide and toluene were removed
  11. customa rotary evaporator
  12. distillationthe reaction mixture was distilled under vacuum
  13. customThe volatile product amounted to 53 g (74% recovered yield)
  14. distillationFractional distillation

Sources & evidence

ORD record
ord-f9b1c60390ef4da5b3d5eee035c28829
Source dataset
uspto-grants-1996_01
Patent number
US05486545

Reaction notes

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