Sodium Hydroxide → (3R)-2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoic acid

Temperature

40 °C

3.0 g of (3R)-ethyl 2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoate (about 88% pure, about 9.16 mmol; diastereomer mixture) were dissolved in a mixture of 12.4 ml each of methanol, THF and water, and 5.49 g (137.35 mmol) of sodium hydroxide were added a little at a time. The reaction mixture was stirred at 40° C. for 9 h. After cooling, the volatile solvents were substantially removed under reduced pressure, and the residue was diluted with water. The mixture was acidified by addition of hydrochloric acid, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure, and the residue was dried under high vacuum. This gave 2.61 g of the title compound as a crude product which was not purified any further (diastereomer ratio about 9:1).

1. additionwere added a little at a time
2. temperatureAfter cooling
3. customthe volatile solvents were substantially removed under reduced pressure
4. additionthe residue was diluted with water
5. additionThe mixture was acidified by addition of hydrochloric acid
6. extractionthe aqueous phase was extracted three times with ethyl acetate
7. dry with materialThe combined organic phases were dried over sodium sulphate
8. concentrationconcentrated under reduced pressure
9. customthe residue was dried under high vacuum
10. customThis gave 2.61 g of the title compound as a crude product which was not purified any further (diastereomer ratio about 9:1)

ORD record

ord-57a5a5392e014802b41d5803ea0afd5e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018258B2