Benzaldehyde → Stilbene

HRID 1046274Notes

Reaction equation

HRID 1046274 reaction equation
[O-]CC.[Na+].CO[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1OC)[CH2:10][C:11]#N.C(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[C:9]1([CH:10]=[CH:11][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[CH:14][CH:15]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 667273,4-DimethoxybenzeneacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 11502Stilbene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round-bottom flask, 380 mg (5.64 mmol, 0.1 eq.) of sodium ethoxide was added to a suspension of 10.0 g (56.43 mmol) of 3,4-dimethoxybenzyl cyanide and 5.99 g (56.43 mmol, 1.0 eq.) of benzaldehyde in 150 mL of ethanol under an argon atmosphere at room temperature while stirring, and the resulting mixture was heated to reflux (the oil bath temperature: 85° C.). After three hours, the disappearance of the raw materials was confirmed, and the resulting reaction liquid was cooled on ice to precipitate a solid. The solid was then collected by suction filtration using a Büchner funnel and a filtering flask, which was then washed with 100 mL of methanol twice. The solid was dried under reduced pressure at 60° C. to give 13.70 g (92%) of light yellow powder.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux (the oil bath temperature
  3. custom85° C.
  4. customthe resulting reaction liquid
  5. temperaturewas cooled on ice
  6. customto precipitate a solid
  7. filtrationThe solid was then collected by suction filtration
  8. washwas then washed with 100 mL of methanol twice
  9. customThe solid was dried under reduced pressure at 60° C.
  10. customto give 13.70 g (92%) of light yellow powder

Sources & evidence

ORD record
ord-f106b33a0d7f42ec8d662b63811f77d6
Source dataset
uspto-grants-2013_10
Patent number
US08569327B2

Reaction notes

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