Beta-Propiolactone → 3-(3-Bromopropoxy)propanoic acid

Temperature

80 °C

To a flask was added 3-bromopropanol (25 mL, 0.28 mol) and β-propiolactone (5.0 mL, 0.07 mol) and the resulting mixture was heated to 80° C. for 14 h. The reaction mixture was then cooled to room temperature and the excess 3-bromopropanol was removed under reduced pressure. The crude product was dissolved in dichloromethane (300 mL) and extracted with 1 N sodium hydroxide (300 mL). The aqueous layer was then acidified to pH 2 and extracted with dichloromethane (300 mL). The organic layer was then washed with water (200 mL), brine (200 mL), dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure to give 9.4 g of the title intermediate, which was used without further purification (64% yield).

1. temperatureThe reaction mixture was then cooled to room temperature
2. customthe excess 3-bromopropanol was removed under reduced pressure
3. dissolutionThe crude product was dissolved in dichloromethane (300 mL)
4. extractionextracted with 1 N sodium hydroxide (300 mL)
5. extractionextracted with dichloromethane (300 mL)
6. washThe organic layer was then washed with water (200 mL), brine (200 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent removed under reduced pressure

ORD record

ord-4ca9a93a337b470aa67bea0ff976fe0c

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080565B2