Benzaldehyde → 4-(2-Phenylvinyl)pyridine, trans-

HRID 343347Notes

Reaction equation

HRID 343347 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[C:9]1(/[CH:8]=[CH:7]/[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 79634-Methylpyridine

Product 1

HCID 6410984-(2-Phenylvinyl)pyridine, trans-Yield 32.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-picoline (18.6 g, 0.2 mol) and benzaldehyde (21.2 g, 0.2mol) in acetic anhydride (125 ml) was stirred under reflux for 24 h. The resulting black solution was evaporated, the residue partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (100 ml) and the liquid phases decanted from the solid residue. The organic layer was washed with sodium carbonate (100 ml), dried (MgSO4), and evaporated to leave a black solid. The solid remaining from the earlier extraction was dissolved in dichloromethane (100 ml), the solution washed with sodium carbonate (75 ml), dried (MgSO4) and evaporated. The combined solid residues were dissolved in methanol (200ml), treated with charcoal, filtered and the filtrate evaporated to leave a brown solid which was triturated with cyclohexane, the suspension filtered and the solid recrystallised from cyclohexane to leave the product as a brown crystalline powder (11.94 g). The combined organic supernatants were chromatographed on silica gel eluting with ethyl acetate/hexanes (7:3) to give a further crop as a yellow solid (6.2 g).

Workup

  1. temperatureunder reflux for 24 h
  2. customThe resulting black solution was evaporated
  3. customthe residue partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (100 ml)
  4. customthe liquid phases decanted from the solid residue
  5. washThe organic layer was washed with sodium carbonate (100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto leave a black solid
  9. extractionThe solid remaining from the earlier extraction
  10. dissolutionwas dissolved in dichloromethane (100 ml)
  11. washthe solution washed with sodium carbonate (75 ml)
  12. dry with materialdried (MgSO4)
  13. customevaporated
  14. dissolutionThe combined solid residues were dissolved in methanol (200ml)
  15. additiontreated with charcoal
  16. filtrationfiltered
  17. customthe filtrate evaporated
  18. customto leave a brown solid which
  19. customwas triturated with cyclohexane
  20. filtrationthe suspension filtered
  21. customthe solid recrystallised from cyclohexane

Sources & evidence

ORD record
ord-e81ccf8081f74f1199d377889d35cea9
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

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