Triethylamine → (2-Oxo-1,3-dioxolan-4-yl)methyl prop-2-enoate

Temperature

0 °C

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.

1. customa similar preparation
2. custom307-321), to a two liter, three necked, round bottomed flask equipped with a paddle stirrer
3. customA drying tube and a nitrogen line were attached to the flask
4. additionTwo addition funnels
5. additionwere charged
6. additionThe addition
7. customof two hours
8. customThe reaction contents
9. filtrationwere filtered through diatomaceous earth
10. filtrationfiltering media
11. washthe solution was washed with cold 5% HCl
12. addition0.3 g of tert-butanol was added
13. dry with materialthe solution was dried over MgSO4
14. filtrationThe solution was filtered
15. customto remove the drying agent
16. additionto stand over a mixture of NaHCO3 and Na2SO4 for two days
17. filtrationThe solution was filtered
18. temperatureWithout heat
19. customthe solvent was removed as completely as possible
20. custom52 g (42%) of a light yellow liquid was recovered

ORD record

ord-1154f674bce442a78c6709a75ebfa8b7

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05580647