Sciencemadness Discussion Board
Not logged in [Login - Register]
Go To Bottom

Printable Version  
Author: Subject: Chloroform in ether synth?
Jackson
Hazard to Others
***




Posts: 189
Registered: 22-5-2018
Location: U S of A
Member Is Offline

Mood: :) Happy about new glassware :)

[*] posted on 11-2-2019 at 08:47
Chloroform in ether synth?


Could chloroform be used in a Williamson ether synthesis? Would a reaction with sodium ethoxide produce something like tri ethoxymethane or would it stop reacting after the first or second ethoxy group was added?
View user's profile View All Posts By User
DavidJR
International Hazard
*****




Posts: 615
Registered: 1-1-2018
Location: Scotland
Member Is Offline

Mood: Anxious

[*] posted on 11-2-2019 at 08:55


Yes, this is one way to produce triethoxymethane, also known as triethyl orthoformate.
View user's profile View All Posts By User
fusso
International Hazard
*****




Posts: 1400
Registered: 23-6-2017
Location: Toaru city, Toaru nation, Asia, Earth, ∥ universe
Member Is Offline

Mood: H2O-PHoBiC

[*] posted on 11-2-2019 at 10:07


Nurdrage made (MeO)3CH in this vid. I believe Et version can be made this way too.
https://www.youtube.com/watch?v=TmUNTkP2nw0




Useful sites:
Balance Chemical Equation: http://www.webqc.org/balance.php
Molecular mass and elemental composition calculator: https://www.webqc.org/mmcalc.php
Solubility table: https://en.wikipedia.org/wiki/Solubility_table
It's not crime if noone finds out - Nyaruko
List of materials made by ScienceMadness users: https://docs.google.com/spreadsheets/d/1nmJ8uq-h4IkXPxD5svnT...
View user's profile View All Posts By User
Jackson
Hazard to Others
***




Posts: 189
Registered: 22-5-2018
Location: U S of A
Member Is Offline

Mood: :) Happy about new glassware :)

[*] posted on 12-2-2019 at 08:46


Could lithium metal be used in substitution for sodium metal? Just because lithium can be obtained from batteries and it's something that I have access to because of that. I could have access to sodium, but I already have lithium so if it can be used that would be preferable.
View user's profile View All Posts By User
fusso
International Hazard
*****




Posts: 1400
Registered: 23-6-2017
Location: Toaru city, Toaru nation, Asia, Earth, ∥ universe
Member Is Offline

Mood: H2O-PHoBiC

[*] posted on 12-2-2019 at 09:38


I think so, the alkali ion is only a counterion and changing it have little effect on nucleophilic substitution.



Useful sites:
Balance Chemical Equation: http://www.webqc.org/balance.php
Molecular mass and elemental composition calculator: https://www.webqc.org/mmcalc.php
Solubility table: https://en.wikipedia.org/wiki/Solubility_table
It's not crime if noone finds out - Nyaruko
List of materials made by ScienceMadness users: https://docs.google.com/spreadsheets/d/1nmJ8uq-h4IkXPxD5svnT...
View user's profile View All Posts By User
Sigmatropic
Hazard to Others
***




Posts: 208
Registered: 29-1-2017
Member Is Offline

Mood: No Mood

[*] posted on 12-2-2019 at 11:40


Agree with fusso, Except that the oxygen lithium bond is stronger than sodium oxygen. In my experience*, lithium alkoxide are less potent nucleophiles than sodium alkoxides. Generally requiring additives or polar aprotic solvents to work, if I recall the short literature search I did at the time.

*in the comparison between the two step procedure of an organolithium with a benzophenone in THF, acidic work-up to the alcohol then NaH/DMF, alkyl tosylate to give an ether and the single pot procedure of organolithium, benzophenone, then alkyl tosylate all in THF, which after isolation gave the alcohol as the primary product.
Could've been the solvent during alkylation, could've been the difference between sodium and lithium.

[Edited on 12-2-2019 by Sigmatropic]
View user's profile View All Posts By User

  Go To Top