Water → (2,2,2-trifluoroethoxy)acetic acid

To a 3-neck 2-liter round-bottom flask equipped with a mechanical stirrer, reflux condenser and addition funnel was added sodium hydride (60% dispersion in mineral oil) (41.70 g, 1.043 moles) and 1000 ml of toluene under nitrogen. 2,2,2-Trifluoroethanol (52.02 g, 0.520 moles) was added dropwise and this mixture was stirred at room temperature for 0.5 hours. A solution of bromoacetic acid (72.45 g, 0.520 moles) in 100 ml of toluene was then added dropwise and the resulting mixture heated at reflux for 48 hours. After cooling the mixture to room temperature, water (250 ml) was added and the layers separated. The aqueous layer was washed with ether (3×75 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 a yellow oil. Distillation of this oil gave 31.6 g of the product as a colorless oil, bp 110°-118° C./16 mm.

1. customTo a 3-neck 2-liter round-bottom flask equipped with a mechanical stirrer
2. temperaturereflux
3. additioncondenser and addition funnel
4. temperaturethe resulting mixture heated
5. temperatureat reflux for 48 hours
6. temperatureAfter cooling the mixture to room temperature
7. customthe layers separated
8. washThe aqueous layer was washed with ether (3×75 ml)
9. extractionThe resulting mixture was extracted with ether (3×100 ml)
10. washthe combined extracts washed with saturated sodium chloride solution (1×75 ml)
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated in vacuo
13. customto give a yellow oil
14. distillationDistillation of this oil

ORD record

ord-f6ad5bc58459490ea1121045660ed973

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846873