Reaction #76414

Reaction equation

4,4′-methanediyl-bis-benzenediazonium tetrafluoroborate

allyl cyanide

water

→

4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile

Yield 61.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Otherprepared
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Washwashed with water, brine
4. 4
   Dryingdried over MgSO4
5. 5
   Otherevaporated
6. 6
   OtherThe crude beige product is recrystallized from 130 ml of ethanol

Procedure

A suspension of 4,4′-methanediyl-bis-benzenediazonium tetrafluoroborate (11.9 g, 0.03 mol), prepared according to the method of example 6.1, allyl cyanide (8.05 g; 0.12 mol), and palladium acetate (0.135 g, 0.6 mmol) in 80 ml of ethanol is heated at 40° C. during 22 h. The heterogeneous reaction mixture is poured into 300 ml of water, extracted with ethyl acetate, washed with water, brine, dried over MgSO4, and evaporated. The crude beige product is recrystallized from 130 ml of ethanol, yielding 5.44 g (61%) of 4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile as light beige crystals, melting point 128-130° C.

Source