Acetic Acid → 1,1,1-Trifluoro-5-hydroxy-2-pentanone

A 500 mL three neck round bottom flask, fitted with reflux condenser, heating mantle, and magnetic stirrer was charged with 61.5 g (0.31M) of 2,3,4,5-tetrahydro-2-oxo-3-(2,2,2-trifluoro-1,1-dihydroxyethyl)furan, 6.4 mL of concentrated HCl, 10 mL of water, and 80 mL of acetic acid. The reaction mixture was heated at 125 C. overnight. An additional 3.0 mL of concentrated HCl and 5.0 mL of water was added and the reaction mixture was heated for an additional 10 hour. The reaction was partitioned between water and ethyl ether while the water layer was neutralized with solid sodium bicarbonate (100 g). The ether solution was washed with water (2×20 mL), dried (anhydrous MgSO4), and solvent removed under reduced pressure to give 60 g (45%) of a pale yellow oil. nmr(CDCl3)--α2.15 m, 4H), 4.03(m, 1H), 4.20(m, 1H).

1. temperaturewith reflux condenser
2. temperatureheating mantle
3. temperatureThe reaction mixture was heated at 125 C
4. customovernight
5. temperaturethe reaction mixture was heated for an additional 10 hour
6. customThe reaction was partitioned between water and ethyl ether while the water layer
7. washThe ether solution was washed with water (2×20 mL)
8. dry with materialdried (anhydrous MgSO4), and solvent
9. customremoved under reduced pressure

ORD record

ord-ea6d8ff4fa274fbdbe50fd9784617bc2

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04835099