Benzyl Alcohol → Benzonitrile, 4-(hydroxymethyl)-3-methoxy-

HRID 643283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643283
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([Cu])#[N:10].C[CH2:13][O:14]C(C)=O.[NH4+].[Cl-].[NH4+].[OH-]>CN(C=O)C>[OH:8][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:9]#[N:10])=[CH:4][C:3]=1[O:14][CH3:13]

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 21863491Ammonium chloride ammonium hydroxideHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 53997281Benzonitrile, 4-(hydroxymethyl)-3-methoxy-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To the benzyl alcohol prepared in step 1 (0.86 g, 4.0 mmol) in DMF (8 mL) was added CuCN (1.1 g, 12 mmol). The mixture was warmed to 150° C. and stirred for 20 h. The mixture was then cooled to room temperature and EtOAc was added, followed by a saturated NH4Cl/NH4OH solution. The mixture was stirred vigorously for 10 minutes and extracted with EtOAc, then the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography provided 4-hydroxymethyl-3-methoxy-benzonitrile (0.38 g, 2.3 mmol).

Aufarbeitung

  1. temperatureThe mixture was then cooled to room temperature
  2. stirringThe mixture was stirred vigorously for 10 minutes
  3. extractionextracted with EtOAc
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5480febaf5f747acbfebbad6b0d9fafb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700597B2

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