Potassium acrylate → Acryloyloxymethyl 4-acryloyloxybutyl carbonate

Chloromethyl 4-acryloyloxybutyl carbonate (1.183 g, 5.00 mmol) prepared as described in Preparation 9 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 1.24 g (91%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4 H, m, CH2 --CH2), 4.23 (4 H, m, 2× CH2 --O), 5.88 (2 H, s, O--CH2 --O), 5.7-6.8 (6 H, 2×CH=CH2).

1. customas described in Preparation 9
2. customAfter 5 days at 20° C. the solvent is removed under reduced pressure
3. dissolutionthe residue dissolved
4. additionby adding dichloromethane (60 ml) and water (30 ml)
5. customAfter separating the phases the aqueous layer
6. extractionis extracted with dichloromethane (3×30 ml)
7. washthe combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
8. dry with materialThe organic phase is dried (MgSO4)
9. customthe solvent removed under reduced pressure

ORD record

ord-e4fdaf1f2a6947a299651ebe29481173

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05529766