Open Chemistry Journal

2017, 4 : 1-5
Published online 2017 March 23. DOI: 10.2174/1874842201704010001
Publisher ID: CHEM-4-1

RESEARCH ARTICLE
A Simple, Cost-effective Synthesis of Industrially Important Long Chain Primary Alcohols

Robert Milofsky1, * , James Hurley1 , Scott Heston2 , Nicole Hasling1 , Elise Naughton3 and Bruce Stevens

*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: milofsky_r@fortlewis.edu

ABSTRACT

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.

Keywords:

Hydroboration, Oxidation, Alkenes, Alcohols, Regioselectivity.
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