Synthesis of n-hexadecane-I-T

✍ Scribed by P. Adriaens; S. Asselberghs; L. Dumon; B. Meesschaert

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: French
• Weight: 193 KB
• Volume: 16
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580160517

✦ Synopsis

three-;old excess of LiA1H4, cetyl bromide, which is less costly, purer and more stable than cetyl iodide, was chosen for reaction with LiAlT 4 -4 For the synthesis of n-hexadecane-I-T, approximately 5.C mCi of LiAlT (specific activity 237 mCi/mmol; New England Nuclear, Dreieichenhain, West-Germany) was added to a suspension of 711 mg of LiA1H4 (18.75 mmol) in 100 ml of dry THF and refluxed under nitrogen with 7.63 g of cetyl bromide (25.0 mmol) for 26 h. Excess reagent was decomposed with water and the precipitated hydroxides were dissolved in 100 ml of 2N H2S04. The aqueous solution was extracted three times with ether; the combined organic layers were washed with brine and dried over anhydrous Na2S04.

GLC analysis of the ether extract showed a complete conversion into n-hexadecane.

After evaporation of the solvent, the residue of n-hexadecane-1-T (7 ml) was diluted with 159 ml of n-hexadecane and distilled in vacuum to give 159 ml (2225 pCi) of n-hexadecane-I-T with a specific activity of 14.0 uCi/ml.