Reaktion #56535

Reaktionsgleichung

2,4-dichlorobenzyl cyanide

tetrahydrofuran

n-octylbromide

→

α-n-octyl-2,4-dichlorobenzyl cyanide

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenSodium hydride (0.13 moles as a 50% dispersion in mineral oil) is washed with 100 ml
2. 2
   Sonstigeof dry n-hexane to remove the mineral oil
3. 3
   workup.ADDITIONTo this sodium hydride suspension is added dropwise at room temperature
4. 4
   workup.ADDITIONWhen the addition
5. 5
   Sonstigethe resultant reaction mixture
6. 6
   Extraktionextracted with (3×200 ml.) of ether
7. 7
   WaschenThe combined ether extracts are washed, with water, dilute hydrochloric acid, saturated sodium, bicarbonate solution saturated sodium chloride solution
8. 8
   Trocknendried over magnesium sulfate
9. 9
   SonstigeThe solvent is evaporated
10. 10
    Sonstigeto give 39.8 g

Vorschrift

Sodium hydride (0.13 moles as a 50% dispersion in mineral oil) is washed with 100 ml. of dry n-hexane to remove the mineral oil, then blanketed with dry nitrogen and suspended in 250 ml. of freshly distilled tetrahydrofuran. To this sodium hydride suspension is added dropwise at room temperature, a solution of 2,4-dichlorobenzyl cyanide (25 g., 0.13 mole) dissolved in 100 ml. of tetrahydrofuran. When the addition is completed the temperature is maintained at 30° C. for an additional 0.5 hours. A solution of n-octylbromide (27 g., 0.14 mole) is then added dropwise and the resultant reaction mixture is stirred at 40° C. overnight under nitrogen. The reaction mixture is poured into 1 liter of water and extracted with (3×200 ml.) of ether. The combined ether extracts are washed, with water, dilute hydrochloric acid, saturated sodium, bicarbonate solution saturated sodium chloride solution, and dried over magnesium sulfate. The solvent is evaporated to give 39.8 g. (100%) of product.

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