Methyl iodide → Methyl 2-(4-chloro-3-methylphenoxy)-2-[p-(p-chlorophenoxy)phenyl]propionate

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Reaction Steps

A solution of 0.015 mole of lithium N,N-diisopropylamide (prepared as in example 55) in tetrahydrofuran is chilled to -65° C. to -75° C. To the solution is added methyl (4-chloro-3-methylphenoxy)[p-(p-chlorophenoxy)phenyl]acetate in tetrahydrofuran. To the mixture is added 5 ml of hexamethylphosphoramide and while chilling to -65° C. to -75° C., 4.26 g of methyl iodide is added. After 1 hr., the mixture is allowed to warm to room temperature and stirr overnight. The mixture is poured into water and extracted with ether. The ether extracts are washed with 10% hydrochloric acid, water, saturated NaHCo3, saturated NaCl solution and dried (MgSO4). Evaporation of the solvent under reduced pressure gives the product as an oil.

Provenance & Evidence