Open Chemistry Journal


ISSN: 1874-8422 ― Volume 8, 2021

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.

Keywords: Hydroboration, Oxidation, Alkenes, Alcohols, Regioselectivity.

Article Information

Identifiers and Pagination:

Year: 2017
Volume: 4
First Page: 1
Last Page: 5
Publisher Id: CHEM-4-1
DOI: 10.2174/1874842201704010001

Article History:

Received Date: 14/10/2016
Revision Received Date: 13/01/2017
Acceptance Date: 17/01/2017
Electronic publication date: 23/03/2017
Collection year: 2017

© 2017 Milofsky et al.

open-access license: This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

* 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:

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