5-DODECEN-2-ONE

C. S-Dodeoen-2-one. The 3-carboxy-5-dodecen-2-one (9.0 g, 0.040 mol) is stirred in 150 mL of carbon tetrachloride (Note 16) in a 500-mL, three-necked, round-bottomed flask which is fitted with a reflux condenser, thermometer. Teflon-covered magnetic stirrer, and a ground-glass stopper. After the orange-yellow solution is heated at reflux for 1 hr, TLC analysis shows the reaction to be complete (Note 17). The reaction mixture is concentrated under reduced pressure with warming to afford 7.1 g (0.039 mol, 98%) of a red-orange oil. The product is sufficiently pure for most purposes. It may be purified by vacuum distillation at 105-107°C/2.7 mm (5.2 g, 0.03 mol, 71%) which yields a pale yellow oil (Note 18). 

The method of preparation of 5-dodecen-2-one presented here is a version of the literature procedure published earlier. It offers several advantages over existing methodology (1) The ester enolate modification of the Carroll rearrangement provides the allylic acetoacetates via a mild, fast, and high yield synthesis. This procedure represents a significant Improvement over... 

Reaction progress was followed most accurately by TLC analysis. The disappearance of the baseline material (I.e., 3-carboxy-5-dodecen-2-one) and appearance of the desired ketone at Rf = 0.33 (10% ethyl acetate/llgroln) indicates the completeness of the reaction. 

The Carroll Rearrangement Synthesis of 5-Dodecen-2-one S. R. Wilson and C. E. Augelli, Department of Chemistry,... 

Carbonylative coupling reaction, 68, 116 3-Carboxy-5-dodecen-2-one, (E), 68, 210 Carboxylation, vicinal di-, 68, 41 Carboxylic acids, reduction, 66, 160... 

Stephen R. Wilson and Corinne E. Augelll 210 THE CARROLL REARRANGEMENT 5-DODECEN-2-ONE... 

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