Reacción #2460292

Ecuación de reacción

2-chlorobenzoic acid

4-butoxyphenol

potassium carbonate

HCl

→

2-(4-butoxyphenoxy)benzoic acid

Rendimiento 45.1%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroFirst, 2-(4-butoxyphenoxy)benzoic acid was prepared
2. 2
   Temperaturawas heated
3. 3
   Temperaturaat reflux for 5 h
4. 4
   Temperaturacooled
5. 5
   ExtracciónThe precipitated product was extracted into diethyl ether
6. 6
   OtroThe product was purified by extraction into 5% aqueous NaOH
7. 7
   OtroThe precipitate was collected
8. 8
   Lavadowashed with water
9. 9
   Secadodried in vacuo over CaSO4

Procedimiento

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.

Fuente