3
$\begingroup$

I'm having a Grignard reaction between a ketone or aldehyde with RMgX in mind. The average workup uses water to hydrolize the intermediate alkoxide. But could this intermediate be used without isolation to prepare an ether or ester? For example by simple addition of RX, tosyl chloride, acetyl chloride ...

I don't know if the compoud is reactive enough, however. But it is an alkoxide and you probably wouldn't even need additional base for e.g. HCl scavenging. Maybe someone here knows more about the reactivity or maybe there are some literature examples?

Improve this question
$\endgroup$

1 Answer 1

Reset to default
2
$\begingroup$

Alkoxide, unless hydrolysed, acts as a very good base and is even used for the synthsis of ethers. However the alkoxide obtained in this case will have a yield that is quite low since the O- anion forms a salt as OMgX, hindering its ability to attack the alkyl group R-X. Thus, it is generally avoided.

Improve this answer
$\endgroup$
2
  • $\begingroup$ You could always do a transmetallation by treating with excess LiCl and then work up with your alkyl halide. $\endgroup$
    – Eli Jones
    Commented Nov 20, 2020 at 22:46
  • $\begingroup$ Transmetallation is very good idea. It can be done without much effort. One can simply even add NaCl and then proceed ahead $\endgroup$
    – Adiboy
    Commented Nov 21, 2020 at 1:19

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.