Sciencemadness Discussion Board

Use of decyltriethylammonium iodide in ether synthesis in PiHKAL?

thors.lab - 18-8-2020 at 14:13

In PiHKAL #30 and #37 (and probably others, I was just flipping through randomly), Sasha uses what I believe to be the Williamson ether synthesis to alkylate the alcohol groups on the ring forming the ethers.

He adds, for example, 3,6-dihydroxybenzonorbornane with K2CO3 as the base and methyl iodide in acetone to form the 3,6-dimethoxybenzonorbornane. However, he also adds a small amount of decyltriethylammonium iodide to the reaction. Why is this there? What purpose does this serve?

Metacelsus - 18-8-2020 at 14:42

Hmm, usually this is a phase transfer catalyst. Maybe this helps dissolve the K2CO3 in the organic phase?

thors.lab - 18-8-2020 at 15:20

Quote: Originally posted by Metacelsus  
Hmm, usually this is a phase transfer catalyst. Maybe this helps dissolve the K2CO3 in the organic phase?


Neat, thanks!