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3-Methoxyphenol → HCID 58442552, compound

HRID 1480689
Notes
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Reaction equation

HRID 1480689 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][O:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=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][O:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][CH:28]=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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 90073-MethoxyphenolHCID 62657Potassium Phosphate, TribasicHCID 534028641-(4-chloro-2,6-dimethylphenyl)ethanone

Product 1

HCID 58442552HCID 58442552, compoundYield 73%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

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 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-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, 3H), 6.57-6.56 (m, 2H), 3.79 (s, 3H), 2.48 (s, 3H), 2.22 (s, 6H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered through a small pad of Celite
  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

Sources & evidence

ORD record
ord-89993459506f4b6db9a30ea9acb79099
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409902B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes