반응 #836589

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6-Bromohexanenitrile

Phenethyl alcohol

Water

ethyl acetate

→

title intermediate

수율 104.3%

6-phenethyloxyhexanenitrile

수율 104.3%

용매

sodium hydroxide

tetrahydrofuran

—

hexanes

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후처리

1. 1
   기타resulting in a precipitate
2. 2
   workup.DISSOLUTIONdissolved
3. 3
   온도then cooled to room temperature
4. 4
   workup.WAITleft for 11 days
5. 5
   기타the mixture partitioned
6. 6
   세척The organics were washed with water, saturated sodium chloride
7. 7
   건조dried over sodium sulfate
8. 8
   기타evaporated to dryness

실험 절차

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.

출처