Methyl iodide → 4-Chloro-2-ethylbenzoic acid

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Reaction Steps

The starting material is prepared as follows: To the ice-cooled, stirred solution of 9.6 ml of diisopropylamine in 200 ml of tetrahydrofuran, 42 ml of 1.6 molar butyl lithium in hexane are slowly added, followed by the solution of 5.1 g of 4-chloro-2-methylbenzoic acid in 60 ml of tetrahydrofuran. The mixture is stirred for 15 minutes at 0°, then cooled to -70° and 7.5 ml of methyl iodide are slowly added. It is allowed to warm to 0°, quenched with water, the aqueous layer separated and acidified with concentrated hydrochloric acid. It is extracted with methylene chloride, the extract dried and evaporated, to yield the 4-chloro-2-ethylbenzoic acid.

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