Cross-Metathesis approach to a,w-Bifunctional Compounds from Methyl Oleate and cis-2-Butene-1,4-diol

27 May 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The cross metathesis (CM) of methyl oleate (1) and cis-2-butene-1,2-diol (2) was investigated to access alpha, omega-bifunctional compounds. The optimal CM conditions involve Stewart-Grubbs catalyst at 0 °C, delivering CM product 3 in excellent yield. 3 was converted, in a single step and in >90% yields, to alcohol 7, aldehyde 8, and olefin 10, the useful synthetic intermediates for many specialty chemicals, including PA11 precursor. A tandem CM/isomerization process was also demonstrated for the first time.


olefin metathesis
cross metathesis
methyl oleate
polyamide 11
nylon 11

Supplementary materials

Electronic supporting information
This supporting information include: 1) Experimental sectioin 2) An alternative route to Methyl 11-aminoundecanoate from Methyl 11- hydroxyundecanoate 3) Metathesis catalyst screening 4) Additional studies on allyl alcohol isomerization to aldehyde 5) Ruthenium-catalyzed isomerization of Methyl (E)-11-hydroxyundec-9-enoate to Methyl 11-oxoundecanoate 6) Cross-metathesis / allyl alcohol isomerization – one-pot procedure 7) 1H and 13C NMR spectra


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.