Allyl bromide → 1-[(Prop-1-en-1-yl)oxy]-4-[(prop-2-en-1-yl)oxy]butane

HRID 1288647Notes

Reaction equation

HRID 1288647 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])=[CH:2][CH3:3].[CH2:10](Br)[CH:11]=[CH2:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH:10]=[CH:11][CH3:12])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 543508994-[(Prop-1-en-1-yl)oxy]butan-1-ol

Product 1

HCID 539198551-[(Prop-1-en-1-yl)oxy]-4-[(prop-2-en-1-yl)oxy]butaneYield 75%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 20 g 4(1-propenoxy)-1-butanol (0.15 moles), 24.2 g allyl bromide (0.2 moles), 1.26 g tetra-n-butylammonium bromide (3.9 mmoles); 8 g sodium hydroxide (0.2 moles); and 60 mL toluene were stirred at 60° C. for ten hours. After cooling, the reaction mixture was filtered to remove inorganic salts and the filtrate was poured into distilled water. The organic layer was separated and the aqueous layer was washed again with fresh toluene. The toluene layers were combined and the solvent removed on a rotary evaporator leaving 1-allyloxy-4(1-propenoxy)butane (an α-allyloxy-ω-(1-propenoxy)alkane) as a clear oil. Further purification was accomplished by distillation at 110° C. under a vacuum of 0.7 mm Hg, obtaining a 75% yield.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customto remove inorganic salts
  4. additionthe filtrate was poured
  5. distillationinto distilled water
  6. customThe organic layer was separated
  7. washthe aqueous layer was washed again with fresh toluene
  8. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-343ebebd0b604f3faad4a4fee20173aa
Source dataset
uspto-grants-1998_05
Patent number
US05747172

Reaction notes

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