Reaction #3778

Reaction equation

Amyl alcohol

2,3-dimethoxyphenol

2'-bromoacetophenone

potassium carbonate

→

2-(2,3-dimethoxyphenoxy)acetophenone

Yield 87.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperatureby heating
2. 2
   Washthe resulting solution was washed in dilute hydrochloric acid, in water
3. 3
   Dryingin a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvents therein were distilled off under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:1)

Procedure

Amyl alcohol (44 ml) was added to 2,3-dimethoxyphenol (5 g), 2'-bromoacetophenone (7 g), potassium carbonate (6.7 g) and copper acetate (1.1 g), followed by heating and stirring at 150° C. for 8 hours for reacting them together. To the reaction solution was added ethyl acetate (300 ml), and the resulting solution was washed in dilute hydrochloric acid, in water, and in a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvents therein were distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:1), to recover 2-(2,3-dimethoxyphenoxy)acetophenone (7.6 g; yield of 87%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Source