Potassium Iodide → Methyl alpha-(4-chloro-5,6,7,8-tetrahydro-1-naphthyloxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Beteiligte Stoffe

Reaktionsschritte

To a solution of 1.19 g of sodium methoxide, 4.57 g of 4-chloro-5,6,7,8-tetrahydro-1-naphthol, and 100 mg of potassium iodide was added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture was heated at reflux overnight, cooled to room temperature, and poured into 100 ml of water. The mixture was then extracted with 2 × 75 ml of ether. The combined extracts were washed with 2 × 50 ml of 5% NaOH, 2 × 50 ml of water, 50 ml of saturated brine, and dried (MgSO4). Evaporation of the solvent yielded an oil which was chromatographed over 100 g of silica gel (benzene). Concentration of cuts yielded a yellow gum which solidified on standing to give the product as a white solid, mp 87.5°-90° C (6.4 g).

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