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Author: Subject: Use of decyltriethylammonium iodide in ether synthesis in PiHKAL?
thors.lab
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[*] posted on 18-8-2020 at 14:13
Use of decyltriethylammonium iodide in ether synthesis in PiHKAL?


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?




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Metacelsus
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[*] posted on 18-8-2020 at 14:42


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



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thors.lab
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[*] posted on 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!




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