1
$\begingroup$

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?

$\endgroup$

1 Answer 1

2
$\begingroup$

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.

$\endgroup$

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.