Bromoacetic Acid → 99116-02-6

To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer, reflux condenser and addition funnel was added 500 ml of 2-butanol under nitrogen. Sodium spheres (3.31 g, 0.144 moles) were then added and the mixture heated at reflux for 6 hours and then stirred at room temperature overnight. A solution of bromoacetic acid (10.00 g, 0.072 moles) in 10 ml of 2-butanol was then added dropwise and the mixture stirred at room temperature for 24 hours. The mixture was then concentrated in vacuo to remove the 2-butanol and the resulting white solid dissolved in 100 ml of water. This aqueous solution was washed with ether (2×50 ml) and then acidified to pH 1 with concentrated hydrochloric acid. The resulting mixture was extracted with ether (3×100 ml) and the combined extracts washed with saturated sodium chloride solution (1×50 ml), dried over magnesium sulfate and concentrated in vacuo to give 8.1 g of the product as a pale yellow oil.

1. customTo a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer
2. temperaturereflux
3. additioncondenser and addition funnel
4. additionwere then added
5. temperaturethe mixture heated
6. temperatureat reflux for 6 hours
7. stirringthe mixture stirred at room temperature for 24 hours
8. concentrationThe mixture was then concentrated in vacuo
9. customto remove the 2-butanol
10. dissolutionthe resulting white solid dissolved in 100 ml of water
11. washThis aqueous solution was washed with ether (2×50 ml)
12. extractionThe resulting mixture was extracted with ether (3×100 ml)
13. washthe combined extracts washed with saturated sodium chloride solution (1×50 ml)
14. dry with materialdried over magnesium sulfate
15. concentrationconcentrated in vacuo

ORD record

ord-afb23bec9ef94649bcc0d37a7c4d4a55

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846873