Benzaldehyde → 4-(2-Phenylethenyl)pyridine

HRID 236881

Reaction equation

HRID 236881 reaction equation
[NH+: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.N1CCCCC1.[OH-].[Na+]>C(O)(C)C>[CH:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 34343784-Methylpyridinium

Product 1

HCID 1015764-(2-Phenylethenyl)pyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 67.5 parts of the 4-picolinium quaternary salt as in Example 13 but without the acid salt was added 100 parts isopropanol, 32.5 parts benzaldehyde, and one part piperidine. The resulting solution was boiled at reflux two hours, 100 parts 40% sodium hydroxide added, and the heating continued for two hours. The cooled mixture was extracted with chloroform, and the organic phase evaporated to dryness to yield a residue that was recrystallized from methanol-water to give 21 parts 4-styrylpyridine.

Workup

  1. temperatureat reflux two hours
  2. extractionThe cooled mixture was extracted with chloroform
  3. customthe organic phase evaporated to dryness
  4. customto yield a residue that
  5. customwas recrystallized from methanol-water

Sources & evidence

ORD record
ord-34760d1e90e14ea3aa3e2fc44893f46d
Source dataset
uspto-grants-1979_06
Patent number
US04158093

Linked notes

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