Potassium acrylate → 1-Acryloyloxyethyl 4-acryloyloxybutyl carbonate

1-Chloroethyl 4-acryloyloxybutyl carbonate (1.253 g, 5.00 mmol) is added to a suspension of freeze dried potassium acrylate (0.606 g, 5.50 mmol) and 18-crown-6 (0.066 g, 0.25 mmol) in dimethylformamide (50 ml) under a dry N2 atmosphere. After 5 days at 20° C. the solvent is removed under reduced pressure and the residue dissolved by adding dichloromethane (60 ml) and water (30 ml). After separating the phases the aqueous layer is extracted with dichloromethane (3×30 ml) and the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.28 g (89%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.58 (3 H, d, J=5 Hz, CH3 --CH), 1.80 (4 H, m, CH2 --CH2), 4.24 (4 H, m, 2 ×CH2 --O), 5.7-6.7 (6 H, m, 2×CH=CH2), 6.87 (1 H, k, J=5 Hz, CH--CH3).

1. customAfter 5 days at 20° C. the solvent is removed under reduced pressure
2. dissolutionthe residue dissolved
3. additionby adding dichloromethane (60 ml) and water (30 ml)
4. customAfter separating the phases the aqueous layer
5. extractionis extracted with dichloromethane (3×30 ml)
6. washthe combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
7. dry with materialThe organic phase is dried (MgSO4)
8. customthe solvent removed under reduced pressure

ORD record

ord-145298d7f5414445805ae4c719a42c64

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05534250