4-Ethylphenol → HCID 58442373, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:21]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH3:22]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>[CH2:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=2)=[CH:25][CH:24]=1)[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 1-(4-chloro-2,6-dimethylphenyl)ethanone (5.0 g, 27.4 mmol), K3PO4 (11.6 g, 54.7 mmol), 4-ethylphenol (4.01 g, 32.8 mmol) in toluene (54.8 mL) was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (349 mg, 0.82 mmol) and 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-(4-ethylphenoxy)-2,6-dimethylphenyl)ethanone (6.0 g) as yellow oil in 82% yield: 1H NMR (500 MHz, CDCl3) δ 7.17 (d, J=8.5 Hz, 2 H), 6.93 (d, J=8.5 Hz, 2 H), 6.63 (s, 2H), 2.64 (q, J=7.5 Hz, 2 H), 2.47 (s, 3 H), 2.21 (s, 6 H), 1.25 (t, J=75 Hz, 3 H).
Workup
- temperatureThe solution was cooled to room temperature
- filtrationfiltered through a small pad of diatomaceous earth
- washThe cake was washed with ethyl acetate (50 mL)
- concentrationwas concentrated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-c9a5fca3172a46ef916dd24f081bf774
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999983B2
Reaction notes
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