Phenol → Benzyl Phenyl Ether

Participants

Reaction Conditions

Reaction Steps

Phenol (2.836 g, 30 millimoles, Aldrich, 99+%), sodium hydroxide (1.411 g, 35 millimoles, Merck, 97%), and sodium iodide (0.433 g, 3 millimoles, Aldrich, 98%) were dissolved in water (299.19 g). The excess molar concentration of sodium hydroxide of was 0.166. The aqueous phase was introduced into a 3-neck 500 mL reactor immersed in the water bath at 50° C. The mixture consisting of benzyl chloride (3.930 g, 31 millimoles, Aldrich, 97%), Aliquat 336 (2.597 g, 6 millimoles, Aldrich), durene (0.693 g, 5 millimoles, Aldrich, 98%), and toluene (15.02 g, J. T. Baker, ultra-pure). The organic phase:aqueous phase weight ratio was 1:14. The two phase mixture was stirred mechanically (600 rpm) at 50° C. for 90 minutes. The aliquot of the reaction mixture was centrifuged, the phases were separated and the organic phase was injected into a GC column. The yield of benzyl phenyl ether based on the limiting reactant (phenol) was 70%. No byproducts could be detected in the chromatograms representing the reaction mixture.

Provenance & Evidence