4-Phenoxyphenol → HCID 86690874, compound

HRID 1465572Notes

Reaction equation

HRID 1465572 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+].[O:21]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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>[CH3:8][C:6]1[CH:7]=[C:2]([O:34][C:31]2[CH:30]=[CH:29][C:28]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:33][CH:32]=2)[CH:3]=[C:4]([CH3:12])[C:5]=1[C:9](=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 132544-PhenoxyphenolHCID 62657Potassium Phosphate, TribasicHCID 534028641-(4-chloro-2,6-dimethylphenyl)ethanone

Product 1

HCID 86690874HCID 86690874, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(4-chloro-2,6-dimethylphenyl)ethanone (26-1, 5.00 g, 27.4 mmol), K3PO4 (11.6 g, 54.6 mmol), and 4-phenoxyphenol (6.12 g, 32.9 mmol) in toluene (39.1 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. for 4.0 h 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 the combined filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc:hexanes=1:10 as eluant) to give 1-(2,6-dimethyl-4-(4-phenoxyphenoxy)phenyl)ethanone (26-2, 7.70 g) as white solids in 85% yield: 1H NMR (500 MHz, CDCl3) δ 7.34-7.37 (m, 2 H), 7.10-7.13 (m, 1 H), 6.99-7.04 (m, 6 H), 6.65 (s, 2 H), 2.49 (s, 3 H), 2.24 (s, 6 H).

Workup

  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. concentrationthe combined filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (EtOAc:hexanes=1:10 as eluant)

Sources & evidence

ORD record
ord-4cc0d72a109b4f19946af34552cbb6fc
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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