3-Methoxyphenol → HCID 58442552, compound

Temperature

100 °C

To a solution of 1-(4-chloro-2,6-dimethylphenyl)ethanone (5.00 g, 27.4 mmol), K3PO4 (11.6 g, 54.7 mmol), 3-methoxyphenol (4.08 g, 32.9 mmol) in toluene (54.8 mL) was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (349 mg, 0.82 mmol), Pd(OAc)2 (259 mg, 1.15 mmol). The reaction was heated at 100° C. overnight under N2. The solution was cooled to room temperature and filtered through a small pad of diatomaceous earth. The cake was washed with ethyl acetate (50 mL) and combined filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-(4-(3-methoxyphenoxy)-2,6-dimethylphenyl)ethanone (5.4 g) as yellow oil in 73% yield: 1H NMR (500 MHz, CDCl3) δ 7.24 (m, 1H), 6.68-6.66 (m, 3 H), 6.57-6.56 (m, 2 H), 3.79 (s, 3 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 diatomaceous earth
3. washThe cake was washed with ethyl acetate (50 mL)
4. concentrationwas concentrated under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel

ORD record

ord-22928e55a9de46a88d9bc8afa0e0a2ac

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999983B2