Butyl caproyl

Potassium valerate and potassium cenanthylate give the expected mixed hydrocarbon, a decane, as chief product (butyl-caproyl, Wurtz) ... 

Two months later (June 1855) Wurtz announced the successful synthesis of five novel mixed or asymmetric hydrocarbons (ethyl-butyl, ethyl-amyl, butyl-amyl, butyl-caproyl, and methyl-caproyl), all produced by the reaction of iodides of the radicals with sodium metal— e.g., ethyl iodide and butyl iodide react with sodium to yield, inter alia, the new substance ethyl-butyl. This is precisely what Hofmann and Brodie had tried but failed to accomplish, pursuing Williamson s "mixed ether" strategy, in December 1850. It is a testament to Wurtz s experimental artistry that he succeeded. ... 

Dry caproic acid added with stirring during 10-15 min. to 1.2 moles AICI3, heated 15 min. at 70-80°, 2 moles caproyl chloride added dropwise during 0.5 hr., the temp, raised to 110-150° and held there 4-6 hrs. until HCl-evolution ceases, chloroform added, stirring continued until a homogeneous soln. is formed, 15%-sulfuric acid soln. added dropwise followed by water, the organic layer separated, dried, and twice vacuum-distilled 7-butyl-6,8-tridecanedione. Y 65%. F. e. s. V. M. Dziomko and O. V. Ivanov, Zh. Org. Khim. 3, 712 (1967) C. A. 67, 43370. 

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