Silver nitrate reaction with ethyl iodide

Lead tetraacetate is added in small quantities, with stirring, to an ice-cold suspension of 11 g. of ethyl 3-(D-arabino-tetrahydroxybutyl)-5-methyl 4-furoate in 100 ml. of benzene plus 40 ml. of glacial acetic acid. Addition is stopped when there is a positive reaction with potassium iodide-starch paper. The mixture is stirred for a further ten minutes, filtered, and the benzene solution washed twice with water. The benzene layer is then dried with anhydrous sodium sulfate, filtered, and the filtrate evaporated to dryness. The residue (6 g.) is mixed with a solution of 7.5 g. of sodium hydroxide plus 20 g. of silver nitrate in 40 ml. of water, and heated for 40 minutes on a steam bath. The aqueous solution is filtered, acidified to Congo Red while being cooled with ice, and the crystals formed are removed by filtration, washed with ice-cold water, and dried over phosphorus pentoxide in the vacuum desiccator yield, 2.2 g. After recrystallization from water, the product has m. p. 234r-235°. 

The reactivity of the normal alkyl halides varies with the halogen and with the alkyl group the more reactive are those with the smaller number of carbon atoms. The iodides are the most reactive, the chlorides the most inert. Methyl iodide is much used in organic syntheses, as it reacts readily with many substances and serves as a means of introducing the methyl group into such compounds. An alcoholic solution of methyl iodide reacts with a similar solution of silver nitrate in the cold, and silver iodide is formed. With ethyl iodide the reaction proceeds much more slowly, and with the higher alkyl iodides the application of heat is necessary to bring about reaction. 

Strike couldn t find any decent nitroethane synths except for a couple of Chemical Abstract articles. One suggestion is to treat 1.5 moles of Na2C02 with 1 mole of sodium ethylsulfite and 0.0645 moles of K2CO3 at 125-130°C. Another route would be to use silver nitrate and ethyl iodide [8 p119]. This type of reaction has been used to nitrate other paraffins and would probably work. 

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