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

Temperature

65 °C

To a mixture of 4-fluorobenzaldehyde (5 mL, 45.2 mmol), propan-2-one (9.13 mL, 124 mmol), and water (9.5 mL) was added 12 mL of a 1% solution of NaOH in water. The reaction mixture was heated at 65° C. for 2 h. The mixture was then partitioned between EtOAc and ice water, the organic layer separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried with MgSO4 and concentrated under vacuum. The product was obtained as a yellow oil and was used in the next step without further purification (7.93 g, 48.3 mmol, 100% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.54-7.51 (m, 2H), 7.47 (d, 1H), 7.08 (t, 2H), 6.64 (d, 1H), 2.37 (s, 3H).

1. customThe mixture was then partitioned between EtOAc and ice water
2. customthe organic layer separated
3. extractionthe aqueous layer was extracted twice with EtOAc
4. dry with materialThe combined organic layers were dried with MgSO4
5. concentrationconcentrated under vacuum
6. customThe product was obtained as a yellow oil
7. customwas used in the next step without further purification (7.93 g, 48.3 mmol, 100% yield)

ORD record

ord-626102335e8a47ad8ab0d9002fc4737b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674115B2