I understand that phenylacetic acid reacts with $\ce{KSCN}$ can form phenylacetonitrile plus the side product ($\ce{CO2}$ and $\ce{KSH}$). This is Letts nitrile synthesis

However, the problem is to convert phenylacetic acid to 3-phenylpropionitrile. Is that possible? What reagents do we need?


1 Answer 1


You need to add one carbon, the easiest source of this is as CN-.

Three steps.

  1. Reduce phenylacetic acid to 2-phenylethanol (borane.THF is a good way)

  2. Form the tosylate of the alcohol (TsCl, pyridine)

  3. Treat the tosylate with NaCN in DMSO reference here.


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