Iodine → 1-Propanone, 2-methyl-1-(4-methylphenyl)-

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Reaction Steps

24.6 g of 2-bromopropane was added to a mixture of 4.8 g of magnesium, a few crystals of iodine, and 200 ml of ether. To the resulting Grignard reagent was added a solution of 23.4 g of p-tolunitrile in ether, over a 15-minute period at about 30°. The mixture was stirred at room temperature for 32 hours and refluxed for 3 days, then treated with dilute sulfuric acid, cooled and extracted with ether. The ether solution was dried (MgSO4) and stripped of solvent. The resulting liquid product was cooled, unreacted starting material was decanted. The residue was chromatographed (silica gel, methylene chloride) to give 1-(4-methylphenyl)-2-methyl-1-propanone (5A).

Provenance & Evidence