Methanol → 1-[Cyano(p-benzyloxyphenyl)methyl]cyclohexanol

HRID 1874312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874312
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].[C:22]1(=[O:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CCCCCC>[C:16]([CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[C:22]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)#[N:17]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 5228044-Benzyloxyphenylacetonitrile

Produkt 1

HCID 461865381-[Cyano(p-benzyloxyphenyl)methyl]cyclohexanolAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

p-Benzyloxyphenyl acetonitrile (100 g) and methanol (300 ml) was charged into flask Subsequently the reaction mixture was cooled to 0-5° C. and 10% aqueous solution of sodium hydroxide (180 g) and PEG-400 (10 ml) were added. The reaction mixture was then stirred for 30 min. and cyclohexanone (64 g) was added dropwise at 0-5° C. Subsequently, the reaction mass temperature was raised to 25-27° C. and stirred for 15 hours. After completion of the reaction hexane (600 ml) was added, the reaction mixture filtered, washed with hexane (100 ml) followed by DM water to obtain 120 g (83.9%) of the 1-[cyano(p-benzyloxyphenyl)methyl]cyclohexanol.

Aufarbeitung

  1. temperatureSubsequently, the reaction mass temperature was raised to 25-27° C.
  2. stirringstirred for 15 hours
  3. additionwas added
  4. filtrationthe reaction mixture filtered
  5. washwashed with hexane (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-eb37c6964c4e4ae6bb3bf303618c0387
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304578B2

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