6
$\begingroup$

Reaction scheme

How can I convert 1-butyne to 2-phenoxybutanal as shown above? I thought of using a hydroboration-oxidation sequence to introduce the carbonyl group, but I do not know how to add the phenoxy substituent.

$\endgroup$
  • 4
    $\begingroup$ Do you have any ideas about how you might accomplish the transformation, you could edit your post to include these so that people may help you more easily (if they know what exactly you're getting stuck at). Also, welcome! You might find the tour useful to learn more about chem.SE and how the stack exchange format works. $\endgroup$ – NotEvans. Jun 11 '17 at 15:43
  • $\begingroup$ @AshleyAustin Consider using phenol for your addition instead of benzene. Also your product is 2-phenoxy-butanone (not phenyl). $\endgroup$ – A.K. Jun 11 '17 at 15:54
  • $\begingroup$ How would I remove the H of the phenol group then? $\endgroup$ – Ashley Austin Jun 11 '17 at 15:58
  • $\begingroup$ So adding say h2o and phenol and the br- would work? $\endgroup$ – Ashley Austin Jun 11 '17 at 16:09
  • $\begingroup$ Phenol is a pretty decent nucleophile $\endgroup$ – Waylander Jun 11 '17 at 16:19
2
$\begingroup$

Something like this would do: enter image description here

I made the alkene symmetrical so that it would lead to fewer regioselective problems. However, I would advise starting with another starting material as this synthesis might take too long in practice.

| improve this answer | |
$\endgroup$
  • 2
    $\begingroup$ The edited question was wrong, and was not the OP's original question. The target compound was an aldehyde and not a ketone. I have changed it back to what it was supposed to be. $\endgroup$ – orthocresol Jun 14 '17 at 9:19
  • $\begingroup$ I'd strongly recommend updating your answer to reflect that, or else it's technically not an answer. $\endgroup$ – orthocresol Jun 17 '17 at 10:22
2
$\begingroup$
  1. Water, BH3, H2O2, NaOH

This reaction, an hydroboration, yelds butanal

  1. Br2, H2SO4

This reaction, carried without light, is an alpha carbon bromination, and yelds 2-bromobutanal

  1. Sodium phenoxide

This is a simple Williamson Ether Synthesis, which yelds the final product

| improve this answer | |
$\endgroup$
  • 1
    $\begingroup$ The edited question was wrong, and was not the OP's original question. The target compound was an aldehyde and not a ketone. I have changed it back to what it was supposed to be. Of course, this simply means that you just need to take out steps 2 and 3. (However it would also be appreciated if you could add some elaboration as to why you chose this sequence of events.) $\endgroup$ – orthocresol Jun 14 '17 at 9:19
  • $\begingroup$ I'm sorry, the question I answered explicited the request of reagents, without pointing out the reactions (the review " edited Jun 12 at 4:24 by Pritt Balagopal"), and the molecule in that review was a ketone. $\endgroup$ – The_Vinz Jun 15 '17 at 22:11

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

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