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

Temperature

40 °C

3.0 g of ethyl (3R)-2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoate (purity about 88%, about 9.16 mmol; diastereomer mixture) were dissolved in a mixture of in each case 12.4 ml 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, most of the volatile solvents were 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, most of the volatile solvents
3. customwere 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-e4c9d3de5c234443be8060b24f82bdb5

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018414B2