A Simple, Cost-effective Synthesis of Industrially Important Long Chain Primary Alcohols
Robert Milofsky1, *, James Hurley1, Scott Heston2, Nicole Hasling1, Elise Naughton3, Bruce Stevens
1 Department of Chemistry, Fort Lewis College, Durango, CO 81301, USA
2 ACI Technologies, Philadelphia, PA 19113, USA
3 Department of Chemistry, University of Colorado, Colorado Springs, CO 80918, USA
The hydroboration oxidation of high molecular weight α-olefins (C18-C30+) with sodium malonyloxyborohydride (SMB) to generate the corresponding primary alcohols is described. α-Olefins undergo hydroboration upon treatment with sodium borohydride (NaBH4) and malonic acid, methyl malonic acid, dimethyl malonic acid or ethyl malonic acid, and a straightforward oxidation of these alkyl boranes yields the anti-Markovnikov primary alcohols. Following recrystallization in n-hexane, n-octane, n-decane or n-dodecane, the target alcohols were isolated in high purity (>99%). The use of SMB and its derivatives will allow synthesis of larger (C18-C30+) primary alcohols on an industrial scale without the costs and hazards of current methods.
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* Address correspondence to this author at the Department of Chemistry, Fort Lewis College, Durango, CO 81301, USA; Tel: +970-247-7467; Fax: 011-970-247-7567; E-mail: email@example.com