[Bakterien]

I have this molecule : http://www.sigmaaldrich.com/catalog/product/aldrich/447528?lang=en&region=SE

Can I perform a dehydration of the primary alcohol and keep the thiol intact ?

[Bakterien]

I know perform a dehydration of a primary alcohol to the alkene (sulfuric acid, heat). But what will happed to the thiol (primary) ?

[Babcock_Hall]

While we await a reply from a synthetic organic chemist, I am happy to offer two observations.  I am not sure whether or not conditions could be found to dehydrate the alcohol without harming the thiol.  If no such conditions existed, I would protect the thiol (possibly as a thioether), dehydrate, then deprotect the thiol.

[TheUnassuming]

Dehydrate into the corresponding olefin?

[orgopete]

This is hard to say, especially as no structures are provided. Even the dehydration of n-butanol gives a mixture of alkenes, so I'm anticipating a possible mixture just from the alcohol without considering whether the thiol may participate. Will it form a tetrahydrothiophene, etc?

I would argue loss of the thiol is less likely as it is less basic than the alcohol. However, since dehydration of a primary alcohol requires more vigorous conditions, I cannot be certain of how this may affect the thiol.

[billnotgatez]

@Bakterien
I have merged your 2 posts into one
We only post a given question once even if it is worded slightly different
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