[skido123]

Someone tried to make hexylisopropyl ether from hexanol and isopropanol(2-propanol) in the presence of a catalytic amount of H2SO4...
Would this be a good method pf synthesizing the desired product?

[AWK]

No, the main reaction will be elimination of  water from isopropanol

[aldoxime_amine]

No, the main reaction will be elimination of  water from isopropanol

But can't temperature change the course of the reaction, at least theoretically...?

[James Newby]

A much easier way would be to convert one alcohol into a bromine using the Appel reaction (N-bromo succinamide, Triphenyl phosphine), purify then add the other alcohol under non nucleophilic basic conditions

[nj_bartel]

Could also go PBr₃ on the isopropanol and do a williamson synthesis using the sodium hexanolate

[macman104]

nj, it would be much wiser to do it the other way.  In the presence of the base, your secondary bromide will more likely undergo E2 as you are going to form a more stable alkene (in comparison to having the bromide on the hexane chain).

If you reverse them hexyl bromide, and isopropanol, you avoid that issue more (still not full proof), and you also are now doing SN2 on a 1° carbon instead of a 2° one, which is also faster.

[nj_bartel]

Sorry, for some reason I had stuck in my head that a cyclohexyl isopropyl ether was what was being formed, even though I wrote sodium hexanolate.  I don't understand myself.

At any rate, I agree with you.