4-Chlorobenzaldehyde → Stilbene

HRID 745286Notes

Reaction equation

HRID 745286 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[C:5]1([CH:6]=[CH:6][C:5]2[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=2)[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 11502Stilbene

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

29 grams (0.2 mole) of 4-chlorobenzaldehyde were dissolved in 300 ml of absolute dioxane and treated at about 10° C. under nitrogen with 33 ml of TiCl4. There were added 39 grams of zinc dust to the golden suspension whereupon the suspension became a black lilac color. The mixture was heated under reflux for 4-5 hours and after cooling off hydrolyzed with 10% K2CO3 solution and extracted with ether. The organic phase was dried over MgSO4, the solvent rotated off and the stilbene recrystallized.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4-5 hours
  3. extractionextracted with ether
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe stilbene recrystallized

Sources & evidence

ORD record
ord-3c1b9dba691248c1b20d37f8b9a87283
Source dataset
uspto-grants-1986_07
Patent number
US04598091

Reaction notes

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