Acetone → 3-Buten-2-one,4-(3-fluorophenyl)-

Temperature

65 °C

To a mixture of 3-fluorobenzaldehyde (4.0 ml, 37.7 mmol) and acetone (8.86 ml, 121 mmol) in water (10 ml), was added 0.25 M sodium hydroxide (15.08 ml, 3.77 mmol). The reaction mixture was heated at 65° C. for 2 h. The mixture was poured into ice water and extracted with ethyl acetate (200 ml). The organic layer was dried, filtered, and evaporated to give (E)-4-(3-fluorophenyl)but-3-en-2-one as yellow oil. It was used for the next reaction without purification (6.92 g, 42.1 mmol, 112% yield). 1H NMR (CDCl3/400 MHz): δ (ppm) 7.46 (d, 1H), 7.40-7.34 (m, 1H), 7.33-7.29 (m, 1H), 7.26-7.21 (m, 1H), 7.12-7.06 (m, 1H), 6.70 (d, 1H), 2.38 (s, 3H).

1. extractionextracted with ethyl acetate (200 ml)
2. customThe organic layer was dried
3. filtrationfiltered
4. customevaporated

ORD record

ord-7befdcc2e90b49e2a2643972af795cee

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674115B2