Allyl bromide → HCID 11400776, compound

HRID 1108854Notes

Reaction equation

HRID 1108854 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][OH:6])=[CH2:2].[CH2:7](Br)[CH:8]=[CH2:9].[OH-].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1>[CH2:7]([O:6][CH2:5][CH2:4][O:3][CH:1]=[CH2:2])[CH:8]=[CH2:9]

Participants

6

Conditions

Temperature
65 °C

Procedure

A 100 ml round bottom flask fitted with a reflux condenser and a magnetic stirrer was charged with 8.8 grams (0.1 mol) of ethylene glycol monovinyl ether, 14.5 grams (0.12 mol) of allyl bromide, 4.8 grams (0-12 mol) of NaOH, 0.9 grams (3 mol %) of (n-Bu)4NBr, and 20 ml of dried toluene. The white suspension was stirred and heated at 65 ° C. for 12 hours. After cooling the reaction mixture, the resulting light yellow solution was separated from the white solids by decantation and washed with four times with 50 ml portions of water in a separatory funnel. Removal of the solvent under reduced pressure followed by vacuum distillation (b.p. 30° C./0.15 mm Hg gave the desired 1-allyloxy-2-vinyloxyethane as a colorless liquid.

Workup

  1. customA 100 ml round bottom flask fitted with a reflux condenser and a magnetic stirrer
  2. temperatureAfter cooling the reaction mixture
  3. customthe resulting light yellow solution was separated from the white solids by decantation
  4. washwashed with four times with 50 ml portions of water in a separatory funnel
  5. customRemoval of the solvent under reduced pressure
  6. distillationfollowed by vacuum distillation (b.p. 30° C./0.15 mm Hg

Sources & evidence

ORD record
ord-3513aa8e0b77448298c5a9ef374c2db9
Source dataset
uspto-grants-2000_05
Patent number
US06069259

Reaction notes

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