反応 #836589

反応方程式

6-Bromohexanenitrile

Phenethyl alcohol

Water

ethyl acetate

→

title intermediate

収率 104.3%

6-phenethyloxyhexanenitrile

収率 104.3%

溶媒

sodium hydroxide

tetrahydrofuran

—

hexanes

反応条件

後処理

1. 1
   その他resulting in a precipitate
2. 2
   workup.DISSOLUTIONdissolved
3. 3
   温度then cooled to room temperature
4. 4
   workup.WAITleft for 11 days
5. 5
   その他the mixture partitioned
6. 6
   洗浄The organics were washed with water, saturated sodium chloride
7. 7
   乾燥dried over sodium sulfate
8. 8
   その他evaporated to dryness

実験手順

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.

出典