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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.

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    $\begingroup$ 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, 2017 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, 2017 at 15:54
  • $\begingroup$ How would I remove the H of the phenol group then? $\endgroup$ Jun 11, 2017 at 15:58
  • $\begingroup$ So adding say h2o and phenol and the br- would work? $\endgroup$ Jun 11, 2017 at 16:09
  • $\begingroup$ Phenol is a pretty decent nucleophile $\endgroup$
    – Waylander
    Jun 11, 2017 at 16:19

2 Answers 2

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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.

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    $\begingroup$ 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. $\endgroup$ Jun 14, 2017 at 9:19
  • $\begingroup$ I'd strongly recommend updating your answer to reflect that, or else it's technically not an answer. $\endgroup$ Jun 17, 2017 at 10:22
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  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

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    $\begingroup$ 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.) $\endgroup$ Jun 14, 2017 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. $\endgroup$
    – user32223
    Jun 15, 2017 at 22:11

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