How can we convert benzyl alcohol to 2-phenylethanoic acid?

This is what I have tried.
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Can someone tell me whether this is correct because I am not sure about the second reaction.
In my textbook it is given that the following reaction takes place.
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But I am not sure whether the reaction will take place if R' is replaced by H.

Also other methods to convert benzene to 2-phenylethanoic acid are welcome.

  • 1
    $\begingroup$ The reaction of a silver carboxylate salt with an alkyl halide gives a ester, not really useful in this context $\endgroup$
    – Waylander
    Sep 7 '21 at 11:57

One easy way is to do the first step as you have drawn making benzyl chloride, then treat that with KCN (in DMSO or use water/CH2Cl2 with a phase transfer catalyst) to give 2-phenyl acetonitrile then hydrolyse that with aqueous sulfuric acid as described in this Organic Syntheses procedure here

To convert benzene to 2-phenylethanoic acid: benzene reacts with ethylene oxide under Friedel-Crafts conditions to give 2-phenylethanol (see this SE answer here). This is readily oxidised to 2-phenylethanoic acid.

  • $\begingroup$ Is the method which I did correct? $\endgroup$
    – Asher2211
    Sep 7 '21 at 11:30
  • 1
    $\begingroup$ Yes, that will work. Goes even better with a trace of DMF to catalyse it. $\endgroup$
    – Waylander
    Sep 7 '21 at 11:42
  • $\begingroup$ Certainly the formation of benzyl chloride will work but, as @Waylander has pointed out, silver formate will give an ester, benzyl formate. The use of a silver salt here is overkill because potassium or sodium formate would suffice. $\endgroup$
    – user55119
    Sep 7 '21 at 15:31

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