(Triphenylphosphoranylidene)acetaldehyde → 3-Cyano-1-(2-formylethenyl)benzene

HRID 1700282Notes

Reaction equation

HRID 1700282 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].C1(P(=[CH:30][CH:31]=[O:32])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:30][CH:31]=[O:32])[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 90670m-Formylbenzonitrile

Product 1

HCID 544772143-Cyano-1-(2-formylethenyl)benzeneYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-cyanobenzaldehyde (2.0 g) and (triphenylphosphoranylidene) acetaldehyde (5.0 g) in 100 mL CH2Cl2 was stirred at reflux for 16 hours. The reaction was cooled, concentrated and purified on silica gel column (ethyl acetate/hexane=3/7) to afford 2.2 g of 3-cyano-1-(2-formylethenyl)benzene as a yellow oil.

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. custompurified on silica gel column (ethyl acetate/hexane=3/7)

Sources & evidence

ORD record
ord-302567ddfded4a23971f0fe358d863fc
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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