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Synthesis of [5-14C]-dodecane and [8-14C]-hexadecane

✍ Scribed by Torsten Schenk; Burkhard Schmidt

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
344 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

[5‐^14^C]‐Dodecane and [8‐^14^C]‐Hexadecane were synthesized starting with [1‐^14^C]‐octanoic acid. The carboxylic acid was reduced to 1‐octanol, which was esterified to n‐octyl p‐toluenesulfonate. Following a Corey‐House procedure, the sulfonate was either reacted with Li[Cu(butyl)~2~] to [5‐^14^C]‐dodecane (40 % overall yield), or with Li[Cu(octyl)~2~] to [8‐^14^C]‐hexhadecane (24 % overall yield). The lithium di‐alkyl cuprates were prepared from butyl lithium and n‐octyl bromide, respectively. Preliminary experiments with non‐labeled compounds using a wittig reaction as chain extension step, turned out to be less favourable. The Corey‐House route provides a simple method for the synthesis of specifically ^14^C‐labeled alkanes from commercially available [1‐^14^C]‐carboxylic acids.

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