Diethyl Ether → 4-Methoxyethoxymethoxy-iodobenzene

Temperature

0 °C

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.

1. temperaturewarmed to room temperature
2. stirringstirred under nitrogen for 24 hours
3. customThe solvent was removed
4. washwashed with 200 ml of 5% sodium hydroxide (4×200 ml), water (4×200 ml), saturated sodium chloride (1×200 ml)
5. dry with materialdried over sodium sulfate
6. customEvaporation of the solvent under reduced pressure
7. customgave an oily product in 14.1 g

ORD record

ord-a1b2d0e683464eb585672bec5e4b02fc

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07083986B2