4-Chlorophenol → HCID 20392611, compound

Participants

Reaction Steps

To a mixture of 2.38 g of sodium methylate in 80 ml of methanol is added 6.42 g of 4-chlorophenol and a few crystals of potassium iodide. After 1/2 hour of stirring a solution of 14.2 g of methyl α-bromo-α-(p-iodophenyl)acetate in 6 ml of benzene is added. The mixture is refluxed overnight. After cooling to room temperature, the mixture is added to 200 ml of water and extracted with two 50 ml portions of chloroform. The combined organic layers are washed with 50 ml of 5% NaOH, 50 ml of H2O, 50 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent affords the product as a white solid, mp 122°-125° C. A portion is recrystallized from petroleum ether to yield white crystals, mp 126°-127° C.

Provenance & Evidence