Allyl bromide → Ethylene glycol diallyl ether

HRID 2391753Notes

Reaction equation

HRID 2391753 reaction equation
[H-].[Na+].[CH2:3]([O:6][CH2:7][CH2:8][OH:9])[CH:4]=[CH2:5].[CH2:10](Br)[CH:11]=[CH2:12]>>[CH2:3]([O:6][CH2:7][CH2:8][O:9][CH2:12][CH:11]=[CH2:10])[CH:4]=[CH2:5]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 8116Ethylene glycol monoallyl etherHCID 24758Sodium hydride

Product 1

HCID 24151Ethylene glycol diallyl etherYield 83%

Procedure

Sodium hydride (NaH, 5.0 g, 0.208 mol) was slowly added to a solution of 2-allyloxy-ethanol (20 mL, 0.187 mol) while stirring. Allyl bromide (32 mL, 0.370 mol) was added and the mixture was stirred at 60° C. for 10 hours. After cooling, the reaction mixture was filtered and a dark oil was obtained after solvent evaporation. The oil was fractionally distilled to give 22 grams of 3-(2-allyloxy-ethoxy)-propene (0.155 mol, yield 83%) as a colorless oil. 1H NMR (400 Mz, CDCl3): δ 3.6 (t, 2H), 4.0 (d, 2H), 5.1 (d 1H), 5.3 (d 1H), 5.9 (q, 1H).

Workup

  1. stirringthe mixture was stirred at 60° C. for 10 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customa dark oil was obtained
  5. customafter solvent evaporation
  6. distillationThe oil was fractionally distilled

Sources & evidence

ORD record
ord-7e615624f8e741d1b7d5b17057aac106
Source dataset
uspto-grants-2012_09
Patent number
US08274075B2

Reaction notes

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