Phenol → 1-(4-Methoxybenzyloxy)-2-methyl-3-phenoxybenzene

Participants

Reaction Conditions

Reaction Steps

Sodium hydride as a 60% dispersion in mineral oil (56 mg, 1.4 mmol) was added portionwise to a solution of phenol (0.35M in DMF, 2 mL). The resultant solution was added to a mixture of 1-bromo-3-(4-methoxybenzyloxy)-2-methylbenzene (215 mg, 0.7 mmol) and cesium carbonate (228 mg, 0.7 mmol) in a microwave vessel. Copper (I) bromide (10 mg) was added, the vessel was sealed and the reaction heated at 180° C. for 900 s. 1N NaOH (aq) (2 mL) and DCM (5 mL) were added to the cooled reaction mixture and the organic layer was separated and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 5:95 ethyl acetate:heptane afforded 1-(4-methoxybenzyloxy)-2-methyl-3-phenoxybenzene (205 mg, 0.64 mmol, 91%).

Provenance & Evidence