Lithium hydroxide, monohydrate → 4,4,4-Trifluoro-2-methylbutanoic acid

A solution of ethyl 4,4,4-trifluoro-2-methylbutyrate (7.7 g) in methanol (21 mL), tetrahydrofuran (21 mL) and water (8.4 mL) was treated with lithium hydroxide monohydrate (3.5 g). The mixture was stirred for 48 hours and the organic solvents evaporated. The resulting aqueous solution was diluted with water and acidified with 6N hydrochloric acid. The aqueous solution was exhaustively extracted with ethyl acetate. The combined organic extract was washed (water and brine), dried (MgSO4), filtered and evaporated to give 4,4,4-trifluoro-2-methylbutyric acid as a pale yellow liquid (6.5 g, 99%); partial NMR (300 MHz, CDCl3): 1.34 (d, 3H, CH3), 2.18 (m, 1H, H-C(3)), 2.67, (m, 1H, H-C(3)), 2.74 (m, 1H, H-C(2)), 10.6 (br, 1H, CO2H).

1. customthe organic solvents evaporated
2. additionThe resulting aqueous solution was diluted with water
3. extractionThe aqueous solution was exhaustively extracted with ethyl acetate
4. extractionThe combined organic extract
5. washwas washed (water and brine)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated

ORD record

ord-626451fa93894450a258201656956d3c

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05334765