RESEARCH ARTICLE
A Simple, Cost-effective Synthesis of Industrially Important Long Chain Primary Alcohols
Robert Milofsky1, *, James Hurley1, Scott Heston2, Nicole Hasling1, Elise Naughton3, Bruce Stevens
Article Information
Identifiers and Pagination:
Year: 2017Volume: 4
First Page: 1
Last Page: 5
Publisher Id: CHEM-4-1
DOI: 10.2174/1874842201704010001
Article History:
Received Date: 14/10/2016Revision 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: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
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: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
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.
