Allyl Alcohol → 1-Ethenyl-4-{[(prop-2-en-1-yl)oxy]methyl}benzene

HRID 1728432Notes

Reaction equation

HRID 1728432 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].CC1OC1.[Na].[CH:10]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1)=[CH2:11]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:10]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:4][CH2:1][CH:2]=[CH2:3])=[CH:14][CH:13]=1)=[CH2:11]

Participants

6

Reactant 3

HCID 7858Allyl AlcoholHCID 74126p-Vinylbenzyl chlorideHCID 131718528HCID 131718528, compound

Product 1

HCID 190181581-Ethenyl-4-{[(prop-2-en-1-yl)oxy]methyl}benzeneYield 91.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

After 691.0 g (5.0 mole) of a 50% 2-propenyl alcohol solution of sodium 2-propenoxide, 16.0 g of tetrabutylammonium bromide and 1.0 g of BHT were placed and mixed in a 3-liter glass flask equipped with a stirrer, a reflux condenser, a thermometer and a dropping funnel, 763.0 g (5.0 mole) of 4-vinylbenzyl chloride was added dropwise to the mixture from the dropping funnel as the temperature was kept at 35°-40° C. to make them undergo the reaction. At the conclusion of the reaction, water was added to dissolve the produced salt. The resulting organic phase was separated, and then distilled to collect a 83°-84° C./2 mmHg fraction. Thus, 795.4 g of 3-(4-vinylbenzyloxy)-1-propene was obtained in a 91.3% yield.

Workup

  1. additionmixed in a 3-liter glass flask
  2. customequipped with a stirrer, a reflux condenser
  3. customwas kept at 35°-40° C.
  4. customthe reaction
  5. additionwas added
  6. dissolutionto dissolve the produced salt
  7. customThe resulting organic phase was separated
  8. distillationdistilled
  9. customto collect a 83°-84° C./2 mmHg fraction

Sources & evidence

ORD record
ord-903a640baf124b1c8c23d7e482c833d5
Source dataset
uspto-grants-1994_07
Patent number
US05326895

Reaction notes

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