Reaction #80586

Reaction equation

4-chlorophenol

potassium carbonate

2,3-dichloropropene

→

1-(4-chlorophenoxy)-2-chloro-2-propene

Yield 98.0%

Solvents

acetone

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureAfter heating
3. 3
   Temperatureto reflux the reaction mixture for 48 hours
4. 4
   Temperaturethe reaction mixture was cooled
5. 5
   Filtrationfiltered
6. 6
   WashThe residue was washed with more acetone
7. 7
   Concentrationthe combined filtrates were concentrated in vacuo
8. 8
   OtherThe crude pale brown liquid (11.5 g) was chromatographed (silica gel, hexane/ethyl acetate, 85/15)

Procedure

To a mixture of 4-chlorophenol (6.1 g, 47.4 mmol) and potassium carbonate (13.1 g, 94.7 mmol) in acetone (200 mL), 2,3-dichloropropene (6.6 mL, 71 mmol) was added. After heating to reflux the reaction mixture for 48 hours, the reaction mixture was cooled and filtered. The residue was washed with more acetone and the combined filtrates were concentrated in vacuo. The crude pale brown liquid (11.5 g) was chromatographed (silica gel, hexane/ethyl acetate, 85/15) to give 1-(4-chlorophenoxy)-2-chloro-2-propene (8.9 g, 98%) as a white liquid: Anal. Calc'd. for C9H8OCl2 : C, 53.23, H, 3.97. Found: C, 53.09, H, 3.95.

Source