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

Participants

Reaction Steps

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).

Provenance & Evidence