November 27, 2024, 01:42:04 AM
Forum Rules: Read This Before Posting


Topic: Set-up for Transetherification  (Read 2215 times)

0 Members and 1 Guest are viewing this topic.

Offline darkdevil

  • Full Member
  • ****
  • Posts: 197
  • Mole Snacks: +3/-2
Set-up for Transetherification
« on: January 22, 2014, 07:22:15 AM »
Dear experts!,
I am doing a transetherification reaction. (eg. methoxybenzene --> butoxybenzene + MeOH) I can get my product correctly, but with a low yield (~ 35%) I am pretty sure that the by product methanol was not properly removed in my set-up which gave a low yield.
i read papers saying that it is important to remove MeOH to shift the equilibrium to the product, but they didnt mention about the set-up
I know some methods like Calcium chloride to remove MeOH, but how exactly is the set-up???

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Set-up for Transetherification
« Reply #1 on: January 22, 2014, 07:59:12 AM »
Try removing it by distillation, under a slight vacuum.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline TheUnassuming

  • Chemist
  • Full Member
  • *
  • Posts: 461
  • Mole Snacks: +48/-1
Re: Set-up for Transetherification
« Reply #2 on: January 22, 2014, 12:39:10 PM »
I think the most common way would be as discodermolide says.  What are you trying to swap the methyl for?  What solvent/conditions are you using?
When in doubt, avoid the Stille coupling.

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Set-up for Transetherification
« Reply #3 on: January 22, 2014, 02:27:14 PM »
Some of the more interesting questions are about mechanisms. This reaction poses an instance. I am surprised by this result. The phenolic oxygen must be the nucleophile to a protonated butanol, and water the nucleophile to attack the methyl group if methanol is to form. I might have thought these conditions might have led to a simple Friedel-Crafts alkylation. Since this sounds as though the interest in a bulk reaction, I don't know the overall economy of a two step procedure which I would try.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links