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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Preferably, the specific step of preparing diphenylacetonitrile is

Add 133g of mandelonitrile, 600g of benzene to a four-necked bottle with a stirrer, a condenser, and a thermometer. Add 40g of concentrated sulfuric acid with a solute mass fraction of 98% at 40-45 °C, and add half an hour. Then, the reaction is stirred at 40-45 ° C for 1 hour until the reaction of the mandelonitrile is completed; yield was 78%

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]

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

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