Sodium Iodide → HCID 11313625, compound

Participants

Reaction Conditions

Reaction Steps

4-Benzyloxyphenol (60.6 g, 0.3 mole), ethylene carbonate (32.0 g, 0.36 mole) and sodium iodide (2.25 g, 0.015 mole) were placed in a 500 ml, three-necked, round-bottom flask equipped with a mechanical stirrer and a reflux condenser. The reaction mixture was stirred and heated at 155° C. After 5 hours, the reaction mixture was cooled to 110° C. and most of the lower boiling materials were removed under reduced pressure. Then, tetrabutylammonium hydrogen sulfate (4.0 g, 0.12 mole), benzyl chloride (45.0 g, 0.35 mole), toluene (200 ml) and sodium hydroxide (20.0 g, 0.5 mole/40 ml of water) were added to the reaction mixture and the vigorous stirring was continued while the reaction mixture temperature was lowered to 90° C. After overnight at this temperature, the reaction mixture was cooled to room temperature and transferred to a separatory funnel. The toluene layer was separated and the aqueous layer was extracted twice with toluene. Toluene extracts were combined, washed with water, dried, treated with Norit A and filtered. The filtrated was passed through a short column of silica gel and eluted with toluene. Fractions containing the product were collected, combined and concentrated. The residue was recrystallized from methanol. Yield: 72.6 g (72%), White solid, M.P.: 71-73° C.

Provenance & Evidence