Reaction #1747866

Reaction equation

4-iodophenol

benzyl chloride

potassium carbonate

→

4-Iodophenyl benzyl ether

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux temperature
3. 3
   Temperatureheated
4. 4
   Filtrationthe reaction mixture was filtered
5. 5
   ConcentrationThe filtrate was concentrated
6. 6
   Temperaturecooled in an ice bath, in the course of which a solid
7. 7
   Otherprecipitated out
8. 8
   OtherThis was removed by means of a blue-band filter
9. 9
   Otherdried
10. 10
    OtherThe crude product (23.22 g) was recrystallized from 70 ml of ethanol
11. 11
    Otheran m.p. of 61-62° C. (lit. 62° C.)
12. 12
    Otherwere obtained

Procedure

A reaction mixture composed of 21.40 g (95.3 mmol) of 98% 4-iodophenol, 12.19 g (95.3 mmol) of 99% benzyl chloride, 20.73 g (150 mmol) of potassium carbonate and 250 ml of acetone was heated to reflux temperature and heated to boiling for 30 hours. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated and then cooled in an ice bath, in the course of which a solid precipitated out. This was removed by means of a blue-band filter and then dried. The crude product (23.22 g) was recrystallized from 70 ml of ethanol. 17.20 g (58% of theory) of colorless microcrystals having an m.p. of 61-62° C. (lit. 62° C.) were obtained.

Source