Benzaldehyde → HCID 54515570, compound

HRID 1973899Notes

Reaction equation

HRID 1973899 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:7][N:6]=[C:5]([CH3:14])[CH:4]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OC(=O)C)(=O)C>[CH:14]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([CH2:9][CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:7][N:6]=1)=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 21490908HCID 21490908, compound

Product 1

HCID 54515570HCID 54515570, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The starting substance can be manufactured by dissolving 26 g of 4-methoxy-5-isoamyl-2-picoline in 78 ml of benzaldehyde and 86 ml of acetic anhydride and heating the reaction mixture for 16 hours under reflux. After cooling, the mixture is evaporated, treated with 2 N sodium hydroxide solution and extracted with ether. Distillation of the ether residue in a bulb tube in a high vacuum at a temperature of 180°-200° yields 2-styryl-4-methoxy-5-isoamyl-pyridine.

Workup

  1. temperatureheating the reaction mixture for 16 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe mixture is evaporated
  5. additiontreated with 2 N sodium hydroxide solution
  6. extractionextracted with ether
  7. distillationDistillation of the ether residue in a bulb tube in a high vacuum at a temperature of 180°-200°

Sources & evidence

ORD record
ord-6fb68f802dee4b79ab26f5ab3b91ed6b
Source dataset
uspto-grants-1976_12
Patent number
US03998955

Reaction notes

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