Tkuze
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 108
Registered: 8-5-2019
Member Is Offline
|
|
Can MgSO4 be used as a drying agent for MeI?
I need to synthesize methyl iodide for methylation of a carboxylic acid to the corresponding methyl ester. I dont have CaCl2, but i do have MgSO4 and
Na2SO4. Can these anhydrous salts be used to dry the methyl iodide instead of the CaCl2?
|
|
TGSpecialist1
Hazard to Self
![*](images/xpblue/star.gif)
Posts: 53
Registered: 24-12-2017
Member Is Offline
Mood: always tired
|
|
Yes.
|
|
Metacelsus
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 2537
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
Yes. The potential reaction to form dimethyl sulfate is actually more favorable in the reverse direction (notably, MeI can be prepared from dimethyl
sulfate + iodide salt)
Off topic, but is there a reason a simple Fischer esterification wouldn't work? I guess if the compound is acid sensitive that would be a no-go.
|
|
CharlieA
National Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 646
Registered: 11-8-2015
Location: Missouri, USA
Member Is Offline
Mood: No Mood
|
|
I don't understand what dimethyl sulfate has to do with it?
Yes, anhydrous MgSO4 or anhydrous Na2SO4 are commonly used as drying agents (especially since MgSO4, Epsom salts, is readily available and
inexpensive).
|
|
Amos
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 1406
Registered: 25-3-2014
Location: Yes
Member Is Offline
Mood: No
|
|
What on earth are you making a methyl ester of that requires you to use such an expensive, hard-to-prepare, and sought-after reagent like methyl
iodide?
|
|
morganbw
National Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 561
Registered: 23-11-2014
Member Is Offline
Mood: No Mood
|
|
Take care with the methyl iodide, its boiling point is pretty low.
Useful though.
|
|
draculic acid69
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 1371
Registered: 2-8-2018
Member Is Offline
|
|
Not exactly hard to prepare I'd say.
|
|
Tsjerk
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 3027
Registered: 20-4-2005
Location: Netherlands
Member Is Offline
Mood: Mood
|
|
Quote: Originally posted by Amos ![](images/xpblue/lastpost.gif) | What on earth are you making a methyl ester of that requires you to use such an expensive, hard-to-prepare, and sought-after reagent like methyl
iodide? |
Something that doesn't like acid catalysts I guess.
|
|
Tkuze
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 108
Registered: 8-5-2019
Member Is Offline
|
|
Its required to make a methy ester, then directly react with concentrated ammonia and ammonium chloride to form an amide. This is for a project in
which the reagent is used to make novel 2-[(diphenylmethyl)sulfinyl] acetamides from the correspondonding carboxylic acid.
Thanks for the help. I only see CaCl2 being used and I have plenty of other drying agents.
|
|
Tsjerk
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 3027
Registered: 20-4-2005
Location: Netherlands
Member Is Offline
Mood: Mood
|
|
Pfff, in that case I wouldn't dare to say other agents would be fine. I can only say sulfates are fine as long as you don't try to dry small alcohols.
Either you have few references or there is a reason to use CaCl2.
|
|
Tkuze
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 108
Registered: 8-5-2019
Member Is Offline
|
|
I agree, there are many other ways of performing this reaction, but there is only one reference in all of scifinder referencing this series of
compounds and their synthesis. The goal is to replicate their results exactly to have a good handle on the chemistry and keep the results consistent.
This is essentially our means of making a control, then we will expand on the library of compounds they created.
|
|
Tkuze
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 108
Registered: 8-5-2019
Member Is Offline
|
|
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3041981/
|
|