Reaction #6705

Reaction equation

ether

methoxyethoxymethyl chloride

4-iodophenol

sodium hydride

→

4-Methoxyethoxymethoxy-iodobenzene

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturewarmed to room temperature
2. 2
   workup.STIRRINGstirred under nitrogen for 24 hours
3. 3
   OtherThe solvent was removed
4. 4
   Washwashed with 200 ml of 5% sodium hydroxide (4×200 ml), water (4×200 ml), saturated sodium chloride (1×200 ml)
5. 5
   Dryingdried over sodium sulfate
6. 6
   OtherEvaporation of the solvent under reduced pressure
7. 7
   Othergave an oily product in 14.1 g

Procedure

A solution of 4-iodophenol (10 g, 45.45 mmol) in 200 ml of anhydrous tetrahydrofuran was treated at 0° C. with sodium hydride (2.36 g, 60% dispersion, 59.09 mmol) for 5 minutes. To the resulting mixture was slowly added over a 5-minute period methoxyethoxymethyl chloride (8.3 ml, 72.73 mmol). The mixture was stirred at 0° C. for 30 minutes, warmed to room temperature, and stirred under nitrogen for 24 hours. The solvent was removed under reduce pressure. The residue was taken into 500 ml of ether, washed with 200 ml of 5% sodium hydroxide (4×200 ml), water (4×200 ml), saturated sodium chloride (1×200 ml), and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gave an oily product in 14.1 g. TLC (silica gel, ether): Rf 0.5.

Source