Sodium Cyanide → 2-Naphthylacetonitrile

HRID 333285

Reaktionsgleichung

Reaktionsgleichung von HRID 333285
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1>O.CCO>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[CH2:5][C:1]#[N:2]

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 703202-Bromomethylnaphthalene

Produkt 1

HCID 820082-NaphthylacetonitrileAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of sodium cyanide (10.5 g, 0.214 mol) in H2O (20 mL) was added a solution of 2-(bromomethyl)naphthalene (40.0 g, 0.181 mol) in EtOH (170 mL). The resulting mixture was heated at reflux for 3 h, then spin-evaporated in vacuo. The residue was partitioned between H2O (175 mL) and CH2Cl2 (200 mL). The aqueous layer was further extracted with CH2Cl2 (3×200 mL). The combined organic layers were dried over MgSO4 (5 g) and spin-evaporated in vacuo to a solid. The solid was dissolved in refluxing EtOH (100 mL). The clarified solution was stored at 3° C. for 16 h. Solids were collected by filtration and dried to constant weight in vacuo to give 24.8 g (81.9%) of product suitable for further transformation. A total of 257.2 g of material was prepared in this fashion.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 h
  3. customspin-evaporated in vacuo
  4. customThe residue was partitioned between H2O (175 mL) and CH2Cl2 (200 mL)
  5. extractionThe aqueous layer was further extracted with CH2Cl2 (3×200 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4 (5 g)
  7. customspin-evaporated in vacuo to a solid
  8. dissolutionThe solid was dissolved
  9. temperaturein refluxing EtOH (100 mL)
  10. filtrationSolids were collected by filtration
  11. customdried to constant weight in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b40f0041b9894f6ca5053ad00b45bc74
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877975B2

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