Reaktion #1166471

Reaktionsgleichung

acryloyl chloride

glycerol carbonate

triethylamine

→

(2-Oxo-1,3-dioxolan-4-yl)methyl Acrylate

Lösungsmittel

benzene

dioxane

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea similar preparation
2. 2
   Sonstige307-321), to a two liter, three necked, round bottomed flask equipped with a paddle stirrer
3. 3
   SonstigeA drying tube and a nitrogen line were attached to the flask
4. 4
   workup.ADDITIONTwo addition funnels
5. 5
   workup.ADDITIONwere charged
6. 6
   workup.ADDITIONThe addition
7. 7
   Sonstigeof two hours
8. 8
   SonstigeThe reaction contents
9. 9
   Filtrationwere filtered through diatomaceous earth
10. 10
    Filtrationfiltering media
11. 11
    Waschenthe solution was washed with cold 5% HCl
12. 12
    workup.ADDITION0.3 g of tert-butanol was added
13. 13
    Trocknenthe solution was dried over MgSO4
14. 14
    FiltrationThe solution was filtered
15. 15
    Sonstigeto remove the drying agent
16. 16
    workup.ADDITIONto stand over a mixture of NaHCO3 and Na2SO4 for two days
17. 17
    FiltrationThe solution was filtered
18. 18
    TemperaturWithout heat
19. 19
    Sonstigethe solvent was removed as completely as possible
20. 20
    Sonstige52 g (42%) of a light yellow liquid was recovered

Vorschrift

Following a similar preparation as described by D'Alelio and Huemmer (J. Poly. Sci., 5, 1967, pp. 307-321), to a two liter, three necked, round bottomed flask equipped with a paddle stirrer and thermometer, was added 87 g (0.74 mol.) of glycerol carbonate, followed by 1000 ml of benzene, 100 ml dioxane and 0.95 g of BHT. A drying tube and a nitrogen line were attached to the flask. Stirring was begun and the heterogeneous mixture was cooled to 0° C. with a brine bath. Two addition funnels were charged as follows: to the first was added 75 g (0.74 mol.) of triethylamine; to the second was added a solution of 100 ml of benzene and 60 g (0.66 mol.) of acryloyl chloride. Two drops of acryloyl chloride solution were added for every one drop of triethylamine. The addition took place over a period of two hours. The reaction contents were filtered through diatomaceous earth filtering media and the solution was washed with cold 5% HCl, followed by four 200 ml portions of water. 0.3 g of tert-butanol was added and the solution was dried over MgSO4. The solution was filtered to remove the drying agent and allowed to stand over a mixture of NaHCO3 and Na2SO4 for two days. The solution was filtered, transferred to a one liter, round bottomed flask and placed on a rotoevaporator. Without heat being applied, a vacuum of approximately 5 mmHg (667 Pa) was applied and the solvent was removed as completely as possible. 52 g (42%) of a light yellow liquid was recovered. 13C NMR identified the liquid to contain 86%, by weight, of the desired compound, the balance being benzene and dioxane.

Quelle