Water → 4-Allyoxystyrene

HRID 1781949Notes

Reaction equation

HRID 1781949 reaction equation
[OH-].[K+].O.[C:4]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1)(=O)[CH3:5].[CH2:16](Br)C=C>O1CCOCC1.C1(C)C=CC=CC=1>[CH2:4]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1)[CH:5]=[CH2:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 117688574-Allyoxystyrene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a 4-necked, nitrogen swept, 2 liter glass reaction vessel equipped with a mechanical stirrer, double-walled condenser, thermocouple and pressure compensating addition funnel is added 1,4-dioxane (600 mls), potassium hydroxide (112.0 g, 2.00 moles) and water (39 g). The mixture is stirred and cooled to 10° C. at which time 4-acetoxystyrene (162.0 g, 1.00 moles) is added over approximately 5 minutes. The mixture is stirred for a further 1.5 hour and cooled to 5° C. A solution of allylbromide (133.1 g, 1.10 moles) in 1,4-dioxane (50 mls) is added dropwise over 15 minutes and the reaction mixture is stirred for a further 1.5 hours, while the temperature is maintained between 5° and 10° C. The stirred mixture is gradually heated to 60° C. Heating and stirring are continued at this temperature for a further 2.5 hours. On cooling the mixture is filtered and most of the solvent is removed under reduced pressure. The residue obtained is dissolved in toluene (300 mls) and the solution washed with 4×300 ml portions of water, dried over sodium sulfate and the solvent distilled under reduced pressure to yield crude 4-allyloxystyrene in high yield.

Workup

  1. customequipped with a mechanical stirrer, double-walled condenser
  2. additionthermocouple and pressure compensating addition funnel
  3. additionis added over approximately 5 minutes
  4. stirringThe mixture is stirred for a further 1.5 hour
  5. stirringthe reaction mixture is stirred for a further 1.5 hours, while the temperature
  6. temperatureis maintained between 5° and 10° C
  7. temperatureThe stirred mixture is gradually heated to 60° C
  8. temperatureHeating
  9. stirringstirring
  10. temperatureOn cooling the mixture
  11. filtrationis filtered and most of the solvent
  12. customis removed under reduced pressure
  13. customThe residue obtained
  14. washthe solution washed with 4×300 ml portions of water
  15. dry with materialdried over sodium sulfate
  16. distillationthe solvent distilled under reduced pressure

Sources & evidence

ORD record
ord-63cf88ed289a47f680735419176263a5
Source dataset
uspto-grants-1997_05
Patent number
US05633411

Reaction notes

Loading…