Phenol → HCID 58442556, compound

Temperature

100 °C

To a solution of 1-(4-chloro-2,6-dimethylphenyl)ethanone (4.50 g, 24.6 mmol), K3PO4 (10.5 g, 49.3 mmol), and phenol (2.78 g, 29.5 mmol) in toluene (49.3 mL) was added 2-(di-tert-butylphosphino)biphenyl (221 mg, 0.74 mmol) and Pd(OAc)2 (233 mg, 1.04 mmol). The reaction was heated at 100° C. for 2.0 h under N2. The solution was cooled to room temperature and filtered through a small pad of Celite. The cake was washed with ethyl acetate (50 mL) and the combined filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-(2,6-dimethyl-4-phenoxyphenyl)ethanone as a yellow oil in 68% yield: 1H NMR (500 MHz, CDCl3) δ 7.35 (t, J=8.0 Hz, 2 H), 7.12 (t, J=7.5 Hz, 1 H), 7.00 (d, J=7.5 Hz, 2 H), 6.65 (s, 2 H), 2.48 (s, 3 H), 2.22 (s, 6 H).

1. temperatureThe solution was cooled to room temperature
2. filtrationfiltered through a small pad of Celite
3. washThe cake was washed with ethyl acetate (50 mL)
4. concentrationthe combined filtrate was concentrated under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel

ORD record

ord-565e07832ad2411aa702151f79eeb965

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946268B2