Allyl bromide → HCID 11400776, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- customA 100 ml round bottom flask fitted with a reflux condenser and a magnetic stirrer
- temperatureAfter cooling the reaction mixture
- customthe resulting light yellow solution was separated from the white solids by decantation
- washwashed with four times with 50 ml portions of water in a separatory funnel
- customRemoval of the solvent under reduced pressure
- 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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