反应 #2460292

ord-bc8a5c16748542c89324f2e12269afa9

反应方程式

O=C(O)c1ccccc1Cl
2-chlorobenzoic acid
CCCCOc1ccc(O)cc1
4-butoxyphenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
Cl
HCl
CCCCOc1ccc(Oc2ccccc2C(=O)O)cc1
2-(4-butoxyphenoxy)benzoic acid
收率 45.1%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他First, 2-(4-butoxyphenoxy)benzoic acid was prepared
  2. 2
    温度was heated
  3. 3
    温度at reflux for 5 h
  4. 4
    温度cooled
  5. 5
    萃取The precipitated product was extracted into diethyl ether
  6. 6
    其他The product was purified by extraction into 5% aqueous NaOH
  7. 7
    其他The precipitate was collected
  8. 8
    洗涤washed with water
  9. 9
    干燥dried in vacuo over CaSO4

实验过程

First, 2-(4-butoxyphenoxy)benzoic acid was prepared. A stirred mixture of 2-chlorobenzoic acid (10.0 g, 64 mmol), 4-butoxyphenol (12.7 g, 77 mmol), potassium carbonate (17.6 g, 128 mmol), copper powder (0.24 g, 3.8 mmol), copper (I) iodide (0.20 g, 1.3 mmol), dithioerithritol (0.20 g, 1.3 mmol), and 75 mL of N,N-dimethylformamide was heated at reflux for 5 h and then cooled to ambient. The reaction mixture was poured onto a mixture of 300 g of ice plus 100 mL of 10% aqueous HCl. The precipitated product was extracted into diethyl ether. The product was purified by extraction into 5% aqueous NaOH, followed by acidification with concentrated HCl. The precipitate was collected, washed with water, and dried in vacuo over CaSO4 to provide 8.27 g (45% of theory) of 2-(4-butoxyphenoxy)benzoic acid as a brown powder.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07459263B2uspto-grants-2008_12