Reaktion #2460292

Reaktionsgleichung

2-chlorobenzoic acid

4-butoxyphenol

potassium carbonate

HCl

→

2-(4-butoxyphenoxy)benzoic acid

Ausbeute 45.1%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeFirst, 2-(4-butoxyphenoxy)benzoic acid was prepared
2. 2
   Temperaturwas heated
3. 3
   Temperaturat reflux for 5 h
4. 4
   Temperaturcooled
5. 5
   ExtraktionThe precipitated product was extracted into diethyl ether
6. 6
   SonstigeThe product was purified by extraction into 5% aqueous NaOH
7. 7
   SonstigeThe precipitate was collected
8. 8
   Waschenwashed with water
9. 9
   Trocknendried in vacuo over CaSO4

Vorschrift

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.

Quelle