synthesis of mandelonitrile

[Jack]

If I react 2 bromo 2 phenylacetonitrile with sodium hydroxide in DMSO will I obtain mandelonitrile by nucleophilic substitution?

 

[WillD]

u will get mandelic acid. For what u need mandelonitrile?

 

[Jack]

mandelonitrile reacts in a sulfuric acid catalysed friedel crafts reaction with benzene to form diphenylacetonitrile, It is a hydroxyalkylation.

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Its just my preference to use a easily available catalyst like sulfuric acid instead of Aluminum trichloride.

 

[WillD]

Only purchase of mandelonitrile or synthes from benzaldehyde. This route was devised to circumvent the bromination reaction.

 

[Jack]

For the synthesis of diphenylacetonitrile, can the anhydrous Aluminum trichloride be substituted for anhydrous Iron trichloride instead when reacting alpha bromo phenylacetonitrile with benzene.

 

[WillD]

You can try to use various Lewis acids, the main thing is anhydrous.