Author Topic: Synthesis of Allyl Iodide  (Read 2514 times)

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Synthesis of Allyl Iodide
« on: January 23, 2003, 11:07:00 PM »
The Preparation of Allyl Iodide[1]

Reported methods for the preparation of allyl iodide involve the reaction of allyl alcohol or glycerol with either hydriodic acid or phosphorus and iodine[2]. We find that preparative quantities of allyl iodide may be obtained very conveniently by the action of sodium iodide on allyl chloride in acetone. This preparation is based on a reaction investigated kinetically by Conant, Kirner and Hussey[3].

A mixture made of 0.6 mole (45.9g) of allyl chloride, 0.75 mole (113g) of sodium iodide, and 100ml of acetone was warmed on the steam-bath for three hours and then poured into 500ml of water. The organic layer was separated, washed with both a dilute sodium bisulfite solution and with water, dried over sodium sulfate, and distilled. The yield of allyl iodide (bp 101-102°C) was 63.1g (62.6%). When the reflux time was increased to twenty-four hours and 200ml of acetone was used as solvent, the yield was increased to 76.7%.

[1] JACS 70, 2818 (1938).
[2] JACS  61, 226 (1929); JACS  38, 1076 (1916); JACS  36, 1005 (1914);  Ann., 116, 156 (1870).
[3] JACS  47, 488 (1925).


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« Reply #1 on: January 24, 2003, 08:21:00 PM »
Just for SWIM's personal curiousity, is this a Finkelstein swap?


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Yes sir
« Reply #2 on: January 24, 2003, 08:24:00 PM »
It is a classic example.