Cyclohexanone → 1-(3-Methoxyphenyl)cyclohexan-1-ol

HRID 852629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852629
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[C:11]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CCOCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([OH:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 7967CyclohexanoneHCID 178490745HCID 178490745, Verbindung

Produkt 1

HCID 146851021-(3-Methoxyphenyl)cyclohexan-1-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 3-methoxyphenylmagnesium bromide (1M in THF, 61 ml, 61 mmol, 1 equiv) at 0° C. was slowly added cyclohexanone (6 g, 61 mmol, 1 equiv) in Et2O (30 ml). The resulting mixture was stirred at room temperature for 4 h then poured in H2O at 0° C. The two layers were separated and the aqueous phase was extracted three times with Et2O. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo to give 1-[3-(methyloxy)phenyl]cyclohexanol (D314) (12.4 g, 100%) as a pale yellow oil which was used in the next step without further purification.

Aufarbeitung

  1. customat 0° C.
  2. customThe two layers were separated
  3. extractionthe aqueous phase was extracted three times with Et2O
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0bec0111f2a74284a85df968fbc9f0dc
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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