P-Cresol → Methyl 2-(2-chlorophenyl)-2-(4-methylphenoxy)acetate

Participants

Reaction Steps

To a stirred (0° C.) suspension of 0.530 g (4.63 mmol) of a 35% oil dispersion of potassium hydride in 5 mL of anhydrous DMF was added 0.50 g (4.63 mmol) of p-cresol and 0.050 g of 18-crown-6. After stirring at room temperature for 15 minutes, a solution of 1.22 g (4.63 mmol) of the product of Step B in 5 mL of DMF was slowly added. The reaction mixture was stirred and allowed to warm to room temperature during 45 minutes. The reaction mixture was then partitioned between ethyl acetate and water, separated, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 1.03 g (77%) of the title compound.

Provenance & Evidence