2- Iodoethyl benzoate

Iodoethyl benzoate has been obtained by the action of alcoholic sodium iodide on 2-chloroethyl benzoate. ... 

B. 2-Iodoethyl benzoate. A mixture of 170 g. of anhydrous sodium iodide and 1.2 1. of methyl ethyl ketone (Note 2) is heated on a steam bath for 1 hour with occasional shaking in a 3-1. round-bottomed flask fitted with a water-cooled reflux condenser. 2-Chloroethyl benzoate (162 g., 0.88 mole) is added to the mixture, and heating is maintained for an additional 22-24 hours with occasional shaking. The mixture is cooled to room temperature and filtered through a 15-cm. Buchner funnel with suction. The inorganic salts on the filter are washed with 200 ml. of methyl ethyl ketone, and the filtrate is concentrated by distillation of about 1 1. of the solvent. The residue is poured into 1 1. of water contained in a separatory funnel, which is shaken, and the lower layer is withdrawn. The latter is washed successively with 200 ml. of 10% sodium bisulfite solution, 200 ml. of 5% sodium bicarbonate solution, and 100 ml. of water. It is dried with anhydrous magnesium sulfate (5-7 g.) and fractionated under reduced pressure. The yield of material boiling at 133 -136°/2.5 mm., 1.5820, is 190 -196 g. (78-81%). 

IodocycIohexyl isocyanate, 162 1-lododecane, 112, 313 Iododurene, 163-164 1-Iodoethyl benzoate, 141 Iodoform, 165—166 1-Iodoheptane, 212 Iodohydrins, 159 lodomesitylene, 287... 

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