How can phenoxyacetone be synthesized from phenol?

My Attempt:

We would first need to deprotonate phenol by addition of NaH in THF and then add bromopropene.

I'm not quite sure where I would go from here. Any help would be much appreciated!

  • 1
    $\begingroup$ 1-phenoxy-2-propanone isn't a correct name. Are you referring to this compound as your synthesis would seem to imply? Alternatively it could be this but I'm not sure how your synthesis would get you there. $\endgroup$
    – bon
    Jul 7, 2015 at 17:25
  • $\begingroup$ i was referring to this molecule : sigmaaldrich.com/catalog/product/aldrich/… $\endgroup$
    – Nerdingout
    Jul 7, 2015 at 17:44
  • 1
    $\begingroup$ @Nerdingout Asking questions back and forth in the comments prevents anyone else from benefiting from the information. Please ask a new question rather than turning this into a tutorial! :) Thanks. $\endgroup$
    – jonsca
    Jul 7, 2015 at 23:17
  • 1
    $\begingroup$ @Nerdingout I have rolled back your post to include the question again. It was flagged for unclear what you are asking. I then noticed, that you did quite a bit of destruction in the past. If you do not what to have any help any more, you can try to delete the question, rather than destroying it. Thank you for your kind understanding. $\endgroup$ Jul 8, 2015 at 6:00
  • $\begingroup$ Does not even need to be done in DMF, MeCN or acetone would ber perfectly acceptable and easier to work up $\endgroup$
    – user32431
    Aug 1, 2016 at 20:43

1 Answer 1


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Your suggested method seems excessively complicated. Substitution of chloroacetone with phenol under basic conditions should give O-alkylation in reasonably good yield. The phenol will be deprotonated and the nucleophilic phenoxide ion will then undergo an $S_N2$ reaction with the primary alkyl chloride.


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