Potassium Phosphate, Tribasic → HCID 58442529, 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]1[O:25][C:24]2[CH:26]=[C:27]([OH:30])[CH:28]=[CH:29][C:23]=2[O:22]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>[O:22]1[C:23]2[CH:29]=[CH:28][C:27]([O:30][C:2]3[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=3)=[CH:26][C:24]=2[O:25][CH2:21]1Participants
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), sesamol (4.54 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 Celite. The cake was washed with ethyl acetate (50 mL) and combined filtrate was concentrated under reduced pressure. The residue was recrystallized in MeOH to give 1-(4-(benzo[d][1,3]dioxol-5-yloxy)-2,6-dimethylphenyl)ethanone (4.80 g) as white solids in 62% yield: 1H NMR (500 MHz, CDCl3) δ 6.77 (d, J=8.5 Hz, 1H), 6.59 (s, 2H), 6.56 (s, 1H), 6.48 (m, 1H), 5.98 (s, 2H), 2.46 (s, 3H), 2.21 (s, 6H).
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 recrystallized in MeOH
Sources & evidence
- ORD record
- ord-6870d655563a414894ff3068c259f716
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409902B2
Reaction notes
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