Water → 2-(Tert-butoxy)acetic acid

To a 3-neck 2-liter round-bottom flask equipped with a mechanical stirrer, reflux condenser and addition funnel was added potassium tert-butoxide (100.00 g, 0.891 moles) and 1500 ml of toluene under nitrogen. A solution of bromoacetic acid (61.90 g, 0.446 moles) in 100 ml of toluene was then added dropwise and the mixture then heated at reflux for 24 hours. After cooling the mixture to room temperature, water (100 ml) was added and the layers separated. The aqueous layer 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 (1×75 ml), dried over magnesium sulfate and concentrated in vacuo to give 27.3 g of the product as a yellow oil.

1. customTo a 3-neck 2-liter round-bottom flask equipped with a mechanical stirrer
2. temperaturereflux
3. additioncondenser and addition funnel
4. temperaturethe mixture then heated
5. temperatureat reflux for 24 hours
6. customthe layers separated
7. washThe aqueous layer was washed with ether (2×50 ml)
8. extractionThe resulting mixture was extracted with ether (3×100 ml)
9. washthe combined extracts washed with saturated sodium chloride solution (1×75 ml)
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated in vacuo

ORD record

ord-af6d1240beae43f6a71847c8466acc25

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846873