反应 #1925197

ord-8e3de5a580b04de08d57ed5479561267

反应方程式

O
water
OCCCCCBr
5-bromopentanol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
Oc1ccc(Br)cc1
4-bromophenol
OCCCCCOc1ccc(Br)cc1
5-(4-bromophenoxy)pentanol
收率 76.4%

反应条件

温度
52.5°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他In a flask equipped with a stirrer
  2. 2
    workup.ADDITIONwas added
  3. 3
    萃取the mixture was subjected to extraction with ethyl acetate
  4. 4
    洗涤The resulting organic phase was washed with NaCl saturated water
  5. 5
    干燥dried over anhydrous sodium sulfate
  6. 6
    过滤filtered
  7. 7
    浓缩concentrated
  8. 8
    其他to thereby obtain 7.8 g of a crude product in the form of a yellow oil
  9. 9
    其他The crude product was then purified by silica gel column chromatography

实验过程

In a flask equipped with a stirrer and a thermometer, 4.29 g (24.8 mmol) of 4-bromophenol was dissolved in 40 ml of dry dimethylformamide (abbreviated as DMF hereinbelow) under a nitrogen atmosphere, and 5.0 g (29.9 mmol) of 5-bromopentanol and 4.14 g (29.9 mmol) of potassium carbonate were added at room temperature, followed by stirring at 50 to 55° C. for 5 hours under incubation. After the completion of the reaction, water was added, and the mixture was subjected to extraction with ethyl acetate. The resulting organic phase was washed with NaCl saturated water, dried over anhydrous sodium sulfate, filtered, and concentrated, to thereby obtain 7.8 g of a crude product in the form of a yellow oil. The crude product was then purified by silica gel column chromatography using hexane/ethyl acetate as an eluting solvent to obtain 4.91 g of 5-(4-bromophenoxy)pentanol in the form of a light yellow oil in a 76% yield.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US06673267B2uspto-grants-2004_01