Sulfuric Acid → 4,4,4-Trifluoro-2-hydroxybutanoic acid

A solution of 2-amino-4,4,4-trifluorobutanoic acid (12-1) (1 g, 6.37 mmol) in 1 N aqueous sulfuric acid (10.00 ml, 10 mmol) was cooled to 0° C. To the cooled reaction mixture was added a solution of sodium nitrite (1.1 g, 15.9 mmol) in water (5 mL) dropwise over 40 minutes via addition funnel. The reaction mixture was then warmed to room temperature and stirred for 16 h. Sodium chloride was added to the reaction until complete saturation was achieved. The resulting aqueous mixture was washed with ethyl acetate (3×50 mL) and the combined organic layer was dried over sodium sulfate, filtered and concentrated to dryness to afford 12-2 as a white crystalline solid. 1H NMR (500 MHz, DMSO-d6) δ 2.51 (m, 1H), 2.67 (m, 1H), 4.24 (dd, J=8.60, 3.60 Hz, 1H), 5.74 (br s, 1H), 12.89 (br s, 1H).

1. customTo the cooled reaction mixture
2. additionvia addition funnel
3. washThe resulting aqueous mixture was washed with ethyl acetate (3×50 mL)
4. dry with materialthe combined organic layer was dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated to dryness

ORD record

ord-097ac9750692471e966df07a3556daab

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428492B2