Reaction #2460292

Reaction equation

2-chlorobenzoic acid

4-butoxyphenol

potassium carbonate

HCl

→

2-(4-butoxyphenoxy)benzoic acid

Yield 45.1%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherFirst, 2-(4-butoxyphenoxy)benzoic acid was prepared
2. 2
   Temperaturewas heated
3. 3
   Temperatureat reflux for 5 h
4. 4
   Temperaturecooled
5. 5
   ExtractionThe precipitated product was extracted into diethyl ether
6. 6
   OtherThe product was purified by extraction into 5% aqueous NaOH
7. 7
   OtherThe precipitate was collected
8. 8
   Washwashed with water
9. 9
   Dryingdried in vacuo over CaSO4

Procedure

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.

Source