I need to know which method to use to synthesize propyl-2-(2-methylpropyl)-ether.

I considered electrophilic addition of alcohols to alkenes, but I'm not really sure how the method works, and anything I found on it was hard to understand. From my understanding I need to "add" electrophilically activated alkenes to alcohol.

I don't really know what that means. I was thinking of using t-butanol and propylene, but the whole part of electrophilically activated alkenes threw me off. Any advice or help is greatly appreciated!

  • $\begingroup$ Electrophilic addition simply means whatever you are adding across your alkene is electrophilic. For example, in the acid-catalyzed addition of water across an alkene, the hydronium acts as an electrophile and hence is being added to the alkene electrophillically in the rate-determining step. The alkene is NOT the electrophile in an electrophilic addition, it is the nucleophile. This might be where you are confused. $\endgroup$ – Eli Jones May 19 '20 at 16:57
  • 2
    $\begingroup$ What is "propyl-2-(2-methylpropyl)-ether" supposed to mean? It doesn't resemble any valid IUPAC name. Do maybe mean 2-methyl-1-propoxypropane? $\endgroup$ – user7951 May 19 '20 at 17:00
  • $\begingroup$ I think what OP meant is t-Bu-O-Pr. $\endgroup$ – Mathew Mahindaratne May 20 '20 at 0:54
  • $\begingroup$ Thing is i think we might use different ways to write chemical names in sweden, which is where im from. $\endgroup$ – quicksilver May 20 '20 at 5:53

There are two basic choices here if you are trying to do this on a lab scale. The alcohol plus alkene with catalytic acid is not an approach I would consider unless I needed a lot of this. t-BuOH plus acid is a recipe for isobutylene. Sodium or potassium t-butoxide is commercially available and reacted with an excess of iPr-I should give a decent yield of the ether.

The other approach is to use t-Butyl 2,2,2-trichloroacetimidate compound details here - a general reagent for the formation of t-Butyl ethers originally reported by Armstrong et al, Tet. Letts 29 2483 (1988)


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