Hydrochloric Acid → 2-(4-Methoxyphenyl)cyclohexanone

HRID 418913

Reaktionsgleichung

Reaktionsgleichung von HRID 418913
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]2=[O:16])=[CH:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 77304-BromoanisoleHCID 7967CyclohexanoneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 2542922-(4-Methoxyphenyl)cyclohexanoneAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Combine 4-bromoanisole (19.6 g, 104 mmol), cyclohexanone (13.2 g, 136 mmol), sodium tert-butoxide (11.8 g, 120 mmol), palladium acetate (0.47 g, 2.1 mmol), (oxy-di-2,1-phenylene)bis-diphenylphosphine (2.28 g, 4.1 mmol) and toluene (240 mL) and heated at 90° C. under nitrogen. After 18 hours, cool to room temperature and add 1N HCl (120 mL). Extract with methylene chloride and wash the combined extracts with brine. Dry the organic layer over sodium sulfate and concentrate in vacuo. Purify by flash chromatography using silica gel and 10% ethyl acetate-hexanes to yield the titled compound (8.15 g, 38%) as a white solid. 1H NMR (CDCl3) δ 7.12 (d, 2H, J=7.5 Hz), 6.92 (d, 2H, J=7.5 Hz), 3.84 (s, 3 H), 3.59 (dd, 1H, J=8.0 and 3.5 Hz), 2.60-2.45 (m, 2H), 2.29 (m, 1H), 2.18 (m, 1H), 2.04 (m, 2H), 1.85 (m, 2H). MS m/z 205 (M+1).

Aufarbeitung

  1. extractionExtract with methylene chloride
  2. washwash the combined extracts with brine
  3. dry with materialDry the organic layer over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customPurify by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3913baa3e50e4a58b0542ab5d19ebd54
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

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