Reaktion #836589

Reaktionsgleichung

6-Bromohexanenitrile

Phenethyl alcohol

Water

ethyl acetate

→

title intermediate

Ausbeute 104.3%

6-phenethyloxyhexanenitrile

Ausbeute 104.3%

Lösungsmittel

sodium hydroxide

tetrahydrofuran

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeresulting in a precipitate
2. 2
   workup.DISSOLUTIONdissolved
3. 3
   Temperaturthen cooled to room temperature
4. 4
   workup.WAITleft for 11 days
5. 5
   Sonstigethe mixture partitioned
6. 6
   WaschenThe organics were washed with water, saturated sodium chloride
7. 7
   Trocknendried over sodium sulfate
8. 8
   Sonstigeevaporated to dryness

Vorschrift

6-Bromohexanenitrile (3.0 mL, 23 mmol) and tetrabutylammonium bromide (350 mg, 1.1 mmol) were dissolved in tetrahydrofuran (5 mL) and 50% aqueous sodium hydroxide (15 mL). Phenethyl alcohol (3.0 mL, 25 mmol) was added resulting in a precipitate. The mixture was heated to 65° C. whereupon the solid dissolved. The mixture was stirred at 65° C. for four hours then cooled to room temperature and left for 11 days. Water, hexanes and ethyl acetate were added and the mixture partitioned. The organics were washed with water, saturated sodium chloride, dried over sodium sulfate and evaporated to dryness to give the title intermediate (5.3 g, 24 mmol) which was used without further purification.

Quelle