Sodium Chloride → 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 chloride (4.0 g, 0.07 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 to 155° C. After 9 hours, the reaction mixture was cooled to 100° C. and most of the lower boiling materials were removed under reduced pressure. Then, tetrabutylammonium hydrogen sulfate (4.0 g, 0.012 mole) and finely powdered potassium hydroxide (28.0 g, 0.5 mole) were added to the reaction mixture and the vigorous stirring was continued. After five minutes, benzyl chloride (45.0 g, 0.36 mole) was added slowly with vigorous stirring. After four hours, toluene (200 ml) and water (60 ml) were added and stirring was continued for another ten minutes. The toluene layer was separated and the aqueous layer was extracted twice with toluene. The in toluene layers were combined and washed with water, dried and concentrated. The residue was recrystallized from methanol. Yield: 82.6 g (82%), White solid, M.P.: 71-73° C.

Provenance & Evidence