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3,5-Dimethylphenol → HCID 58442376, 화합물

HRID 1480686
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HRID 1480686 반응식
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
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참가 물질

7

반응물 3

HCID 79483,5-DimethylphenolHCID 62657Potassium Phosphate, TribasicHCID 534028641-(4-chloro-2,6-dimethylphenyl)ethanone

생성물 1

HCID 58442376HCID 58442376, 화합물수율 86%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매
HCID 11618717
Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane
촉매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

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, 1H), 6.63 (s, 2H), 6.62 (s, 2H), 2.48 (s, 3H), 2.29 (s, 6H), 2.22 (s, 6H).

후처리

  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

출처 및 근거

ORD 기록
ord-c3daf4347eb64fd890e74e20f09136c1
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409902B2

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