Methanol → 4,4,4-Trifluoro-1-(4-methylphenyl)butane-1,3-dione

Temperature

80 °C

Sodium metal (5.76 g, 0.25 mol) was dissolved in methanol (80 ml), then trifluoroacetic acid (22 ml, 0.168 mol) was added at room temperature, followed by dropwise addition of methyl-acetophenone (21.04 g, 0.165 mol). The obtained mixture was stirred at 80° C. for 10 h, the reaction mixture was concentrated in vacuo and the residue was dissolved in water (50 ml). The solution was acidified by addition of 1N hydrochloric acid (120 ml), extracted with ethyl acetate (2×80 ml), dried over MgSO4, filtered and concentrated in vacuo to yield 34.60 g (95%) of the title compound. The obtained crystalline product was used in the next step without further purification.

1. concentrationthe reaction mixture was concentrated in vacuo
2. dissolutionthe residue was dissolved in water (50 ml)
3. additionThe solution was acidified by addition of 1N hydrochloric acid (120 ml)
4. extractionextracted with ethyl acetate (2×80 ml)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-9ab80e42e8b34ef6b988f73d078ddf8a

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723370B2