Rhodium
(Chief Bee)
01-23-03 23:07
No 400932
      Synthesis of Allyl Iodide
(Rated as: excellent)
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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 101-102C) 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%.

References:
[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).
 
 
 
 
    catastrophe
(Hive Bee)
01-24-03 20:21
No 401160
      Curiousity  Bookmark   

Just for SWIM's personal curiousity, is this a Finkelstein swap?
 
 
 
 
    SPISSHAK
(Hive Addict)
01-24-03 20:24
No 401161
      Yes sir  Bookmark   

It is a classic example.