3,5-Dimethylphenol → HCID 58442376, compound

HRID 1843764Notes

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+].[CH3:21][C:22]1[CH:23]=[C:24]([OH:29])[CH:25]=[C:26]([CH3:28])[CH:27]=1>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>[CH3:21][C:22]1[CH:23]=[C:24]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[O:29][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1

Participants

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), 3,5-dimethylphenol (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), 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 Celite. 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-(3,5-dimethylphenoxy)-2,6-dimethylphenyl)ethanone (6.3 g) as yellow solids in 86% yield: 1H NMR (500 MHz, CDCl3) δ 6.76 (s, 1 H), 6.63 (s, 2 H), 6.62 (s, 2 H), 2.48 (s, 3 H), 2.29 (s, 6 H), 2.22 (s, 6 H).

Workup

temperatureThe solution was cooled to room temperature
filtrationfiltered through a small pad of Celite
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-c7bd6855d80d4f99b65e0ba528f0c8af
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946268B2

Reaction notes

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