Open Chemistry Journal




ISSN: ― Volume ,
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
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

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.


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: 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.


* 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



Track Your Manuscript:


Endorsements



I am completely satisfied with the service I received from Bentham Science Publishers, right from the submission of our research paper in ‘Open Chemistry’ to its publication in the journal. The reviewers' and editor's comments were very helpful in improving the paper.

I take this opportunity to express my appreciation to the whole team of BSP!


Dr. Arun Kumar Sharma
Govt. P.G. College,
India


Browse Contents



Webmaster Contact: info@benthamopen.net
Copyright © 2020 Bentham Open