Sodium Chloride → 4-(Cyclohexylmethoxy)phenylacetonitrile

HRID 231250

Reaktionsgleichung

Reaktionsgleichung von HRID 231250
C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=1.[CH:23]1([CH2:29]Br)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[Na+].[Cl-]>C(OCC)(=O)C.CN(C)C=O>[CH:23]1([CH2:29][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

8

Edukt 5

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 137636Cyclohexane, (bromomethyl)-

Produkt 1

HCID 200349234-(Cyclohexylmethoxy)phenylacetonitrileAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 1 L round bottom flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 28.4 g anhydrous potassium carbonate (pulverized with mortar and pestle), cesium carbonate (catalytic amount), 4-(hydroxy)phenyl acetonitrile (18.26 g.), cyclohexylmethylbromide (36.4 g.) and dimethylformamide (600 mL). The mixture was heated to reflux and maintained for one week at this temperature under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and saturated aqueous NaCl and ethyl acetate were added. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic fractions were washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated in a rotary evaporator. The crude product was partitioned between equal volumes of hexane and 25% aqueous NaOH. This mixture was stirred under nitrogen atmosphere at room temperature for three days. The aqueous layer was drawn off, and the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give 23 g of 4-(cyclohexylmethoxy)phenylacetonitrile as a yellow solid (73% yield). This material was homogeneous by TLC (CH2Cl2) and was carried on directly to the next step without further purification.

Aufarbeitung

  1. customA 1 L round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. temperaturemaintained for one week at this temperature under a nitrogen atmosphere
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. washThe combined organic fractions were washed with saturated aqueous NaCl
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in a rotary evaporator
  12. customThe crude product was partitioned between equal volumes of hexane and 25% aqueous NaOH
  13. washthe organic layer was washed with saturated aqueous NaCl
  14. dry with materialdried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1a04b3d2a98f4cc5ac0461cf683fc826
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845231

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