Water → 4,4,4-Trifluoro-2,2-dimethylbutanoic acid

To a solution of ethyl 4,4,4-trifluoro-2,2-dimethylbutanoate (426 mg, 2.15 mmol) in MeOH (15 mL) was added a solution of LiOH in H2O (2 N, 5.35 mL, 10.75 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was concentrated and the resulting mixture was diluted with DCM and washed with 3 N HCl. The aqueous layer was extracted twice with DCM. The combined organic layers were dried over MgSO4, filtered and concentrated to yield 4,4,4-trifluoro-2,2-dimethylbutanoic acid as a colorless oil (370 mg, 100% yield). 1H NMR (400 MHz, CDCl3) ppm 1.35 (s, 6H), 2.48 (ABqt, J=12 Hz, 2H).

1. concentrationThe reaction was concentrated
2. additionthe resulting mixture was diluted with DCM
3. washwashed with 3 N HCl
4. extractionThe aqueous layer was extracted twice with DCM
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-04c7059ce90b455f8210facacb052de5

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642576B2